N-acylimino heterocyclic compounds

ABSTRACT

The invention also relates to the use of the N-acylimino heterocyclic compounds, their stereoisomers, their tautomers and their salts, for combating invertebrate pests. Furthermore the invention relates also to methods of combating invertebrate pests, which comprises applying such compounds.

This application is a National Stage application of InternationalApplication No. PCT/EP2014/069900, filed Sep. 18, 2014, which claims thebenefit of U.S. Provisional Application No. 61/879,691, filed Sep. 19,2013.

The present invention relates to N-acylimino heterocyclic compounds,including their stereoisomers, tautomers and salts, and to compositionscomprising such compounds. The invention also relates to the use of theN-acylimino heterocyclic compounds, their stereoisomers, their tautomersand their salts, for combating invertebrate pests. Furthermore theinvention relates also to methods of combating invertebrate pests, whichcomprises applying such compounds.

BACKGROUND OF INVENTION

Invertebrate pests, such as insects, acaridae and nematode pests destroygrowing and harvested crops and attack wooden dwelling and commercialstructures, causing large economic loss to the food supply and toproperty. While a large number of pesticidal agents are known, due tothe ability of target pests to develop resistance to said agents, thereis an ongoing need for new agents for combating animal pests. Inparticular, animal pests such as insects and acaridae are difficult tobe effectively controlled.

EP 259738 discloses compounds of the formula A, which have insecticidalactivity:

where W is a substituted pyridyl radical or a 5- or 6-memberedheterocyclic radical, R is hydrogen or alkyl, T together with the atomsto which it is bound forms a 5- or 6-membered heterocyclic ring, Y isinter alia a nitrogen atom and Z is an electron withdrawing groupselected from nitro and cyano.

Pesticidal compounds, which are similar to those of EP 259738, are knownfrom EP 639569, where the moiety electron withdrawing moiety Z is anelectron withdrawing group such as alkoxcarbonyl, arylcarbonyl,heterocyclic carbonyl, C₁-C₄-alkylsulfonyl, sulfamoyl or C₁-C₄-acyl.

US 2013/0150414 describe, inter alia, pesticidal compounds of theformula B

wherein Ar is an aryl or 5- or 6-membered heterocyclic group, R^(a) ishydrogen or alkyl, Y′ is hydrogen, halogen, a hydroxyl group, an alkylgroup or an alkoxy group and R^(b) is an alkyl group substituted withhalogen or an alkoxy group, optionally substituted with halogen.

Pesticidal compounds, which are similar to those of US 2013/0150414, areknown from WO 2013/129688.

The pesticidal activity of the compounds is not satisfactory. It istherefore an object of the present invention to provide compounds havinga good pesticidal activity, especially against difficult to controlinsects and acarid pests.

SUMMARY OF INVENTION

It has been found that these objects are solved by N-substitutedacyl-imino compounds of the general formula (I) described below, bytheir stereoisomers, their tautomers and their salts. Therefore, thepresent invention relates to N-acylimino compound of formula (I):

wherein

-   -   m is an integer selected from 0, 1, 2, 3, 4, 5 or 6, in        particular 0 or 1;    -   X is O or S, in particular O;    -   Het is a 5 or 6 membered carbon-bound or nitrogen-bound        heterocyclic or heteroaromatic ring, comprising 1, 2, 3, 4 or 5        carbon atoms and 1, 2 or 3 heteroatoms as ring members, which        are independently selected from sulfur, oxygen or nitrogen,        wherein the carbon, sulfur and nitrogen ring members can        independently be partly or fully oxidized, and wherein each ring        is optionally substituted by k identical or different        substituents R⁶, wherein k is an integer selected from 0, 1, 2,        3 or 4;    -   W¹-W²-W³-W⁴ represents a carbon chain group connected to N and        C═N, and thus forming a saturated, unsaturated, or partially        unsaturated 5 or 6 membered nitrogen containing heterocycle,        wherein        -   W¹, W², W³ and W⁴ each individually represent CR^(v)R^(w),            wherein        -   each R^(w) independently from each other, is selected from            the group consisting hydrogen, halogen, cyano, azido, nitro,            SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,            C₂-C₁₀-alkynyl, and wherein the carbon atoms of the            aforementioned aliphatic and cycloaliphatic radicals may be            unsubstituted or may be partly or fully halogenated and/or            may optionally be substituted with 1, 2 or 3 identical or            different radicals R⁷, OR⁸, NR^(9a)R^(9b), S(O)_(n)R⁸,            S(O)_(n)NR^(9a)R^(9b), C(═O)R^(7a), C(═O)NR^(9a)R^(9b),            C(═O)OR⁸, C(═S)R^(7a), C(═S)NR^(9a)R^(9b), C(═S)OR⁸,            C(═S)SR⁸, C(═NR¹⁷)R^(7a), C(═NR¹⁷)NR^(9a)R^(9b) and            Si(R¹¹)₂R¹²,        -   each R^(v) independently from each other, are selected from            the group consisting of hydrogen, halogen, cyano,            C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl and            C₂-C₁₀-alkynyl, wherein the carbon atoms of the            aforementioned aliphatic and cycloaliphatic radicals may be            unsubstituted or may be partly or fully halogenated or may            optionally be further substituted with 1, 2 or 3 identical            or different radicals R⁷; or        -   R^(v) and R^(w) present in one of the groups may together            form ═O, ═CR¹³R¹⁴, ═S, ═NR¹⁷, ═NOR¹⁶, ═NNR^(9a)R^(9b),            -   or            -   two R^(w) of adjacent carbon atoms, may form both                together and together with the existing bond a double                bond between the adjacent carbon atoms;        -   and wherein one of W² or W³ may optionally represent a            single or a double bond between the adjacent carbon atoms;    -   R¹, R² are independently from each other selected from the group        consisting of hydrogen, halogen, CN, SCN, nitro, C₁-C₆-alkyl,        C₃-C₆-cycloalkyl, wherein each of the two aforementioned        radicals are unsubstituted, partly or completely halogenated or        may carry any combination of 1, 2 or 3 radicals R⁷,        -   Si(R¹¹)₂R¹², OR⁸, OSO₂R⁸, S(O)_(n)R⁸, S(O)_(n)NR^(9a)R^(9b),            NR^(9a)R^(9b), C(═O)NR^(9a)R^(9b), C(═S)NR^(9a)R^(9b),            C(═O)OR⁸, C(═O)R^(7a), C(═S)R^(7a),        -   phenyl, benzyl, where the phenyl ring in the last two            radicals is unsubstituted or optionally substituted with 1,            2, 3, 4 or 5 identical or different substituents R¹⁰,        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 identical or different heteroatoms as ring members, which            are selected from oxygen, nitrogen and sulfur, where the            heterocyclic ring is optionally substituted with 1, 2, 3 or            4 identical or different substituents R¹⁰, and wherein the            nitrogen and/or the sulfur atom(s) of the heterocyclic ring            may optionally be oxidized,        -   or        -   R¹ and R² form, together with the carbon atom, which they            attached to, a 3-, 4-, 5- or 6-membered saturated or partly            unsaturated carbocyclic or heterocyclic ring, wherein each            of the carbon atoms of said cycle are unsubstituted or may            carry any combination of 1 or 2 identical or different            radicals R⁷,        -   or        -   R¹ and R² may together be ═O, ═CR¹³R¹⁴, ═S, ═NR¹⁷, ═NOR¹⁶ or            ═NNR^(9a)R^(9b);    -   R³ is selected from the group consisting of hydrogen, halogen,        CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,        wherein each of the 4 last mentioned radicals are unsubstituted,        partly or completely halogenated or carries 1 or 2 radicals R⁷,        it being also possible for cycloalkyl to carry 1, 2, 3, 4, 5 or        6 C₁-C₄-alkyl groups,        -   S(O)_(n)NR^(9a)R^(9b), NR^(9a)R^(9b), C(═O)OR⁸,            C(═O)NR^(9a)R^(9b), C(═S)NR^(9a)R^(9b), C(═O)R^(7a),            C(═S)R^(7a), NR^(9a)—C(═O)R^(7a), NR^(9a)—C(═S)R^(7a),            NR^(9a)—S(O)_(n)R^(8a),        -   phenyl, benzyl, where the phenyl ring in the last two            mentioned radicals is unsubstituted or may be substituted            with one or more, e.g. 1, 2, 3, 4 or 5 identical or            different substituents R¹⁰,        -   and a 3-, 4-, 5-, 6- or 7-membered saturated, partly            saturated or unsaturated aromatic heterocyclic ring            comprising 1, 2 or 3 heteroatoms as ring members, which are            identical or different and selected from oxygen, nitrogen            and sulfur, where the heterocyclic ring is optionally            substituted with 1, 2, 3 or 4 identical or different            substituents R¹⁰, and wherein the nitrogen and/or the sulfur            atom(s) of the heterocyclic ring may optionally be oxidized;    -   R^(4a), R^(4b) are selected each independently from one another        and independently from the integer of m from the group        consisting of hydrogen, halogen, CN, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-alkylthio, and C₃-C₈-cycloalkyl, wherein each of the 4        last mentioned radicals are unsubstituted, partly or completely        halogenated,        -   or        -   R^(4a) and R^(4b) may form together with the carbon atom            they are bound to, a 3, 4, 5 or 6 membered aliphatic ring,            wherein each of the carbon atoms of the ring may be            unsubstituted or may be partly or fully halogenated, and/or            may carry 1, 2, 3, 4, 5 or 6 radicals selected from            C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and            C₁-C₄-haloalkoxy;        -   or        -   R^(4a) and R^(4b) may together form ═O, ═CR¹³R¹⁴, ═S, ═NR¹⁷,            ═NOR¹⁶, ═NNR^(9a)R^(9b),    -   R⁵ is selected from the group consisting of hydrogen, halogen,        C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,        wherein each of the 4 last mentioned radicals are unsubstituted,        partly or completely halogenated or carries 1 or 2 radicals R⁷,        it being also possible for cycloalkyl radicals to carry 1, 2, 3,        4, 5 or 6 C₁-C₄-alkyl groups,        -   S(O)_(n)NR^(9a)R^(9b), NR^(9a)R^(9b), C(═O)OR⁸,            C(═O)NR^(9a)R^(9b), C(═S)NR^(9a)R^(9b), C(═O)R^(7a),            C(═S)R^(7a), NR^(9a)—C(═O)R^(7a), NR^(9a)—C(═S)R^(7a),            NR^(9a)—S(O)_(n)R^(8a),        -   a moiety Q-phenyl, where the phenyl ring is optionally            substituted with one or more, e.g. 1, 2, 3, 4 or 5 identical            or different substituents R¹⁰,        -   and a moiety Q-Het^(#), where        -   Het^(#) represents a 3-, 4-, 5-, 6- or 7-membered saturated,            partly saturated or unsaturated aromatic heterocyclic ring            comprising 1, 2 or 3 heteroatoms as ring members, which are            selected from oxygen, nitrogen and/or sulfur, where the            heterocyclic ring is optionally substituted with 1, 2, 3 or            4 identical or different substituents R¹⁰, and wherein the            nitrogen and/or the sulfur atom(s) of the heterocyclic ring            may optionally be oxidized, and        -   Q irrespectively of its occurrence, is a single bond,            NR^(9a), NR^(9a)—C₁-C₄-alkylene, —O—C(═O)—, —NR^(9a)—C(═O)—,            —O—S(═O)₂—, —NR^(9a)—S(═O)₂—, —O—C(═O)—C₁-C₄-alkylene or            —NR^(9a)—C(═O)—C₁-C₄-alkylene, where the heteroatom in the            last 6 moieties is bound to the carbon atom of C(CN)R³ or            CR^(4a)R^(4a), respectively;    -   or, if m=0,    -   R³ and R⁵ together may also form with the carbon atom they are        bound to, a 3, 4, 5 or 6 membered saturated partially        unsaturated carbocycle or heterocycle, wherein each of the        carbon atoms of the carbocycle or heterocycle may be        unsubstituted or may be partly or fully halogenated, and/or may        carry 1, 2, 3, 4, 5 or 6 radicals R^(7b), and where the        heterocycle has 1 or 2 non-adjacent identical or different        heteroatoms or heteroatom moieties as ring members, which are        selected from O, S, N and N—R^(17c), or        -   R³ and R⁵ may together form ═O or ═S;    -   where, independently of their occurrence,    -   n is 0, 1 or 2;    -   R⁶ is selected from the group consisting of halogen, cyano,        azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,        C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, and wherein the carbon atoms of        the aforementioned aliphatic and cyclo-aliphatic radicals may        optionally be further substituted independently from one another        with 1, 2 or 3 radicals R⁷,        -   OR⁸, NR^(17a)R^(17b), S(O)_(n)R⁸, S(O)_(n)NR^(17a)R^(17b),            C(═O)R^(7a), C(═O)NR^(17a)R^(17b), C(═O)OR⁸, C(═S)R^(7a),            C(═S)NR^(17a)R^(17b), C(═S)OR⁸, C(═S)SR⁸, C(═NR¹⁷)R^(7a),            C(═NR¹⁷)NR^(17a)R^(17b), Si(R¹¹)₂R¹²;        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different substituents R¹⁰,        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is optionally substituted with            1, 2, 3 or 4 identical or different substituents R¹⁰, and            wherein the nitrogen and/or the sulfur atom(s) of the            heterocyclic ring may optionally be oxidized,        -   or two of R⁶ present on one ring carbon may together form            ═O, ═CR¹³R¹⁴, ═S, ═NR¹⁷, ═NOR¹⁶, ═NNR^(9a)R^(9b),        -   or two R⁶ together form a linear C₂-C₇ alkylene chain, thus            forming, together with the ring atom(s) to which they are            bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2            CH₂ moieties of the alkylene chain may be replaced by 1 or 2            heteroatom moieties selected from O, S and NR^(17c) and/or 1            or 2 of the CH₂ groups of the alkylene chain may be replaced            by a group C═O, C═S and/or C═NR¹⁷; and where the alkylene            chain is unsubstituted or may be substituted with 1, 2, 3,            4, 5 or 6 radicals selected from the group consisting of            halogen, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,            C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl,            C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,            C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl which may be            substituted with 1, 2, 3, 4 or 5 radicals R¹⁰, and a 3-, 4-,            5-, 6- or 7-membered saturated, partially unsaturated or            aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms            or heteroatom groups selected from N, O, S, NO, SO and SO₂,            as ring members, where the heterocyclic ring may be            substituted with 1, 2, 3, 4 or 5 radicals R¹⁰;    -   R⁷ independently of its occurrence, is selected from the group        consisting of cyano, azido, nitro, —SCN, SF₅, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆        haloalkynyl, Si(R¹¹)₂R¹², OR⁸, OSO₂R⁸, S(O)_(n)R⁸,        S(O)_(n)NR^(17a)R^(17b), NR^(17a)R^(17b), C(═O)NR^(17a)R^(17b),        C(═S)NR^(17a)R^(17b), C(═O)OR⁸, C(═O)R¹⁵, C(═S)R¹⁵, C(═NR¹⁷)R¹⁵,        -   phenyl, phenyl-C₁-C₄-alkyl, where the phenyl ring in the            last two groups is optionally substituted with 1, 2, 3, 4 or            5 identical or different substituents R¹⁰, and        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is optionally substituted with            1, 2, 3 or 4 identical or different substituents R¹⁰, and            wherein the nitrogen and/or the sulfur atom(s) of the            heterocyclic ring may optionally be oxidized,        -   or two R⁷ present on one carbon atom may together form ═O,            ═CR¹³R¹⁴, ═S, ═NR¹⁷, ═NOR¹⁶, ═NNR^(9a)R^(9b),        -   or two R⁷ may form a 3-, 4-, 5-, 6-, 7- or 8-membered            saturated or partly unsaturated carbocyclic or heterocyclic            ring together with the carbon atoms to which the two R⁷ are            bonded, where the heterocyclic ring comprises 1, 2 or 3            heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is optionally substituted with            1, 2, 3 or 4 identical or different substituents R¹⁰;    -   R^(7a) independently of its occurrence, is selected from the        group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylthio,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆ haloalkynyl, phenyl,        optionally substituted with 1, 2, 3, 4 or 5 identical or        different substituents R¹⁰, and        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is optionally substituted with            1, 2, 3 or 4 identical or different substituents R¹⁰, and            wherein the nitrogen and/or the sulfur atom(s) of the            heterocyclic ring may optionally be oxidized;    -   R^(7b) is selected from the group consisting of halogen, cyano,        C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,        C₃-C₈-cycloalkenyl, and wherein the carbon atoms of the        aforementioned aliphatic and cycloaliphatic radicals may be        partly or completely halogenated, and/or be substituted with 1,        2 or 3 identical or different radicals R⁷,        -   OR⁸, NR^(17a)R^(17b), S(O)_(n)R⁸, S(O)_(n)NR^(17a)R^(17b),            C(═O)R^(7a), C(═O)NR^(17a)R^(17b), C(═O)OR⁸, C(═S)R^(7a),            C(═S)NR^(17a)R^(17b), C(═S)OR⁸, C(═NR¹⁷)R^(7a),            C(═NR¹⁷)NR^(17a)R^(17b), Si(R¹¹)₂R¹²; phenyl, optionally            substituted with 1, 2, 3, 4 or 5 identical or different            substituents R¹⁰, and        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is optionally substituted with            1, 2, 3 or 4 identical or different substituents R¹⁰, and            wherein the nitrogen and/or the sulfur atom(s) of the            heterocyclic ring may optionally be oxidized,        -   or two of R^(7b) present on one ring carbon may together            form ═O, ═S or ═CR¹³R¹⁴, or two R^(7b) together form a            linear C₂-C₇ alkylene chain, thus forming, together with the            ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7-            or 8-membered ring, where 1 or 2 CH₂ moieties of the            alkylene chain may be replaced by 1 or 2 heteroatom moieties            selected from O, S and NR^(17c) and/or 1 or 2 of the CH₂            groups of the alkylene chain may be replaced by a group C═O,            C═S and/or C═NR¹⁷; and where the alkylene chain is            unsubstituted or may be substituted with 1, 2, 3, 4, 5 or 6            radicals selected from the group consisting of halogen,            C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,            C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl,            C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,            C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl which may be            substituted with 1, 2, 3, 4 or 5 radicals R¹⁰, and a 3-, 4-,            5-, 6- or 7-membered saturated, partially unsaturated or            aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms            or heteroatom groups selected from N, O, S, NO, SO and SO₂,            as ring members, where the heterocyclic ring may be            substituted with 1, 2, 3, 4 or 5 radicals R¹⁰;    -   R⁸ independently of its occurrence, is selected from the group        consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,        C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₂-C₆-alkynyl, C₂-C₆ haloalkynyl, C(═O)R¹⁵,        C(═O)NR^(17a)R^(17b), C(═S)NR^(17a)R^(17b), C(═O)OR¹⁶,        -   phenyl, phenyl-C₁-C₄-alkyl, where the phenyl ring in the            last two mentioned radicals is unsubstituted or substituted            with 1, 2, 3, 4 or 5 identical or different substituents            R¹⁰, and        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is optionally substituted with            1, 2, 3 or 4 identical or different substituents R¹⁰, and            wherein the nitrogen and/or the sulfur atom(s) of the            heterocyclic ring may optionally be oxidized,    -   R^(8a) independently of its occurrence, is selected from the        group consisting of C₁-C₆-alkyl, C₃-C₈-cycloalkyl,        C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,        wherein each of the five last mentioned radicals are        unsubstituted, partly or completely halogenated,        -   phenyl, benzyl, where the phenyl ring in the last two            mentioned radicals is unsubstituted or may be substituted            with one or more, e.g. 1, 2, 3, 4 or 5 identical or            different substituents R¹⁰,        -   and a 3-, 4-, 5-, 6- or 7-membered saturated, partly            saturated or unsaturated aromatic heterocyclic ring            comprising 1, 2 or 3 heteroatoms as ring members, which are            identical or different and selected from oxygen, nitrogen            and sulfur, where the heterocyclic ring is optionally            substituted with 1, 2, 3 or 4 identical or different            substituents R¹⁰, and wherein the nitrogen and/or the sulfur            atom(s) of the heterocyclic ring may optionally be oxidized,    -   R⁹ independently of its occurrence, is selected from the group        consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₈-cycloalkyl,        C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆        haloalkynyl,        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different substituents R¹⁰;        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic C-bound heterocyclic ring comprising            1, 2 or 3 heteroatoms as ring members, which are identical            or different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is optionally substituted with            1, 2, 3 or 4 identical or different substituents R¹⁰, and            wherein the nitrogen and/or the sulfur atom(s) of the            heterocyclic ring may optionally be oxidized,    -   R^(9a), R^(9b) are each independently from one another selected        from the group consisting of hydrogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl,        C₃-C₈-halocycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆        haloalkynyl,        -   S(O)_(n)R¹⁶, —S(O)_(n)NR^(17a)R^(17b), C(═O)R¹⁵, C(═O)OR¹⁶,            C(═O)NR^(17a)R^(17b), C(═S)R¹⁵, C(═S)SR¹⁶,            C(═S)NR^(17a)R^(17b), C(═NR¹⁷)R¹⁵;        -   phenyl, benzyl, 1-phenethyl or 2-phenethyl, where the phenyl            ring in the last four mentioned radicals is unsubstituted or            may be substituted with 1, 2, 3, 4 or 5 identical or            different substituents R¹⁰; and        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic C-bound heterocyclic ring comprising            1, 2 or 3 heteroatoms as ring members, which are identical            or different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is optionally substituted with            1, 2, 3 or 4 identical or different substituents R¹⁰, and            wherein the nitrogen and/or the sulfur atom(s) of the            heterocyclic ring may optionally be oxidized,        -   or,    -   R^(9a) and R^(9b) are together a C₂-C₇ alkylene chain and form a        3-, 4-, 5-, 6-, 7- or 8-membered saturated, partly saturated or        unsaturated aromatic ring together with the nitrogen atom they        are bonded to, wherein the alkylene chain may contain one or two        heteroatoms, which are, independently of each other, selected        from oxygen, sulfur or nitrogen, and where the alkylene chain        may optionally be substituted with 1, 2, 3 or 4 radicals        selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆        haloalkynyl, phenyl, optionally substituted with 1, 2, 3, 4 or 5        identical or different substituents R¹⁰, and a 3-, 4-, 5-, 6- or        7-membered saturated, partly saturated or unsaturated aromatic        C-bound heterocyclic ring comprising 1, 2 or 3 heteroatoms as        ring members, which are identical or different and selected from        oxygen, nitrogen and sulfur, where the heterocyclic ring is        optionally substituted with 1, 2, 3 or 4 identical or different        substituents R¹⁰, and wherein the nitrogen and/or the sulfur        atom(s) of the heterocyclic ring may optionally be oxidized,        -   or    -   R^(9a) and R^(9b) together may form ═CR¹³R¹⁴, ═NR¹⁷, ═NOR¹⁶,        ═NNR^(17a)R^(17b) moiety;    -   R^(9c), R^(9d) are each independently from one another selected        from the group consisting of hydrogen, C₁-C₆-alkyl,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆ haloalkynyl,        S(O)_(n)R¹⁶, —S(O)_(n)NR^(17a)R^(17b), C(═O)R¹⁵, C(═O)OR¹⁶,        C(═O)NR^(17a)R^(17b), C(═S)R¹⁵, C(═S)SR¹⁶, C(═S)NR^(17a)R^(17b),        C(═NR¹⁷)R¹⁵;        -   phenyl, benzyl, where the phenyl ring in the last two            mentioned radicals is unsubstituted or may be substituted            with 1, 2, 3, 4 or 5 identical or different substituents            R¹⁰; and        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic C-bound heterocyclic ring comprising            1, 2 or 3 heteroatoms as ring members, which are identical            or different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is optionally substituted with            1, 2, 3 or 4 identical or different substituents R¹⁰, and            wherein the nitrogen and/or the sulfur atom(s) of the            heterocyclic ring may optionally be oxidized;    -   R¹⁰ independently of its occurrence, is selected from the group        consisting of halogen, cyano, azido, nitro, SCN, SF₅,        C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,        wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may optionally be substituted with 1, 2,        3, 4 or 5 identical or different radicals R^(10a),        -   Si(R¹¹)₂R¹², OR¹⁶, OS(O)_(n)R¹⁶, —S(O)_(n)R¹⁶,            S(O)_(n)NR^(17a)R^(17b), NR^(17a)R^(17b), C(═O)R¹⁵,            C(═S)R¹⁵, C(═O)OR¹⁶, —C(═NR¹⁷)R¹⁵, C(═O)NR^(17a)R^(17b),            C(═S)NR^(17a)R^(17b),        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different radicals selected from OH, halogen,            cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and            C₁-C₆-haloalkoxy, and        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is unsubstituted or may be            substituted with 1, 2, 3, 4 or 5 substituents selected            independently from one another from halogen, cyano, NO₂,            C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and            C₁-C₆-haloalkoxy, and wherein the nitrogen and/or the sulfur            atom(s) of the heterocyclic ring may optionally be oxidized;        -   or        -   two R¹⁰ present together on one carbon ring atom of a            saturated or partly unsaturated heterocyclic radical may            form ═O, ═CR¹³R¹⁴, ═S, ═NR¹⁷, ═NOR¹⁶, ═NNR^(17a)R^(17b);        -   or,        -   two R¹⁰ on adjacent carbon ring atoms may also be a bivalent            radical selected from CH₂CH₂CH₂CH₂, CH═CH—CH═CH, N═CH—CH═CH,            CH═N—CH═CH, N═CH—N═CH, OCH₂CH₂CH₂, OCH═CHCH₂, CH₂OCH₂CH₂,            OCH₂CH₂O, OCH₂OCH₂, CH₂CH₂CH₂, CH═CHCH₂, CH₂CH₂O, CH═CHO,            CH₂OCH₂, CH₂C(═O)O, C(═O)OCH₂, O(CH₂)O, SCH₂CH₂CH₂,            SCH═CHCH₂, CH₂SCH₂CH₂, SCH₂CH₂S, SCH₂SCH₂, CH₂CH₂S, CH═CHS,            CH₂SCH₂, CH₂C(═S)S, C(═S)SCH₂, S(CH₂)S, CH₂CH₂NR¹⁷, CH₂CH═N,            CH═CH—NR¹⁷, OCH═N, SCH═N and form together with the carbon            atoms to which the two R¹⁰ are bonded to a 5-membered or            6-membered partly saturated or unsaturated, aromatic            carbocyclic or heterocyclic ring, wherein the ring may            optionally be substituted with one or two substituents            selected from ═O, OH, CH₃, OCH₃, halogen, cyano, halomethyl            and halomethoxy;    -   R^(10a) independently of its occurrence, is selected from the        group consisting of halogen, cyano, NO₂, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, Si(R¹¹)₂R¹², OR¹⁶, OS(O)_(n)R¹⁶,        —S(O)_(n)R¹⁶, S(O)_(n)NR^(17a)R^(17b), NR^(17a)R^(17b),        C(═O)R¹⁵, C(═S)R¹⁵, C(═O)OR¹⁶, —C(═NR¹⁷)R¹⁵,        C(═O)NR^(17a)R^(17b), C(═S)NR^(17a)R^(17b),        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different radicals selected from OH, halogen,            cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and            C₁-C₆-haloalkoxy;    -   R¹¹, R¹² independently of their occurrence, are selected from        the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,        C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl-C₁-C₄-alkyl,        C₁-C₆-haloalkoxy-C₁-C₄-alkyl, phenyl and benzyl, where the        phenyl ring in last two radicals are unsubstituted or        substituted with 1, 2, 3, 4 or 5 identical or different radicals        selected from halogen, OH, cyano, NO₂, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;    -   R¹³, R¹⁴ independently of their occurrence, are selected from        the group consisting of hydrogen, halogen, CN, C₁-C₆-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl;    -   R¹⁵ independently of its occurrence, is selected from the group        consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, wherein the four last mentioned        aliphatic and cycloaliphatic radicals may be unsubstituted,        partially or fully halogenated and/or oxygenated and/or may        carry 1 or 2 radicals selected from C₁-C₄ alkoxy;        -   phenyl, benzyl and pyridyl, wherein the last three radicals            may be unsubstituted, partially or fully halogenated and/or            to carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy,            (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)amino or            di-(C₁-C₆-alkyl)amino;    -   R¹⁶ independently of its occurrence, is selected from the group        consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,        wherein the five last mentioned aliphatic and cycloaliphatic        radicals may be unsubstituted, partially or fully halogenated        and/or oxygenated and/or may carry 1 or 2 radicals selected from        C₁-C₄ alkoxy,        -   phenyl, benzyl and pyridyl, wherein the last three radicals            may be unsubstituted, partially or fully halogenated and/or            to carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy,            (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)amino or            di-(C₁-C₆-alkyl)amino;    -   R¹⁷ independently of its occurrence, is selected from the group        consisting of hydrogen, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, trimethylsilyl, triethylsilyl,        tertbutyldimethylsilyl,        -   C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,            wherein the four last mentioned aliphatic and cycloaliphatic            radicals may be unsubstituted, partially or fully            halogenated and/or oxygenated and/or may carry 1 or 2            radicals selected from C₁-C₄-alkoxy,        -   phenyl, benzyl, pyridyl, phenoxy, wherein the four last            mentioned radicals may be unsubstituted, partially or fully            halogenated and/or carry 1, 2 or 3 substituents selected            from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆            haloalkoxy and (C₁-C₆-alkoxy)carbonyl,    -   R^(17a), R^(17b) are each independently from one another        selected from the group consisting of hydrogen, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylthio, trimethylsilyl,        triethylsilyl, tertbutyldimethylsilyl,        -   C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,            wherein the four last mentioned aliphatic and            cyclo-aliphatic radicals may be unsubstituted, partially or            fully halogenated and/or oxygenated and/or may carry 1 or 2            radicals selected from C₁-C₄-alkoxy,        -   phenyl, benzyl, pyridyl, phenoxy, wherein the four last            mentioned radicals may be unsubstituted, partially or fully            halogenated and/or carry 1, 2 or 3 substituents selected            from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆            haloalkoxy and (C₁-C₆-alkoxy)carbonyl,        -   or,        -   R^(17a) and R^(17b) may together be a C₂-C₆ alkylene chain            forming a 3- to 7-membered saturated, partly saturated or            unsaturated ring together with the nitrogen atom R^(17a) and            R^(17b) are bonded to, wherein the alkylene chain may            contain 1 or 2 heteroatoms selected, independently of each            other, from oxygen, sulfur or nitrogen, and may optionally            be substituted with halogen, C₁-C₄-haloalkyl, C₁-C₄-alkoxy            or C₁-C₄-haloalkoxy, and wherein the nitrogen and/or the            sulfur atom(s) of the heterocyclic ring may optionally be            oxidized;        -   or    -   R^(17a) and R^(17b) together may form ═CR¹³R¹⁴, ═NR¹⁷ or ═NOR¹⁶        moiety;    -   R^(17c) independently of its occurrence, is selected from the        group consisting of hydrogen, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,        wherein the five last mentioned aliphatic and cycloaliphatic        radicals may be unsubstituted, partially or fully halogenated        and/or oxygenated and/or may carry 1 or 2 radicals selected from        C₁-C₄ alkoxy,        -   phenyl, benzyl and pyridyl, wherein the last three radicals            may be unsubstituted, partially or fully halogenated and/or            to carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy,            (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)amino or            di-(C₁-C₆-alkyl)amino;    -   the stereoisomers, the tautomers and the salts thereof.

Moreover, the present invention relates to and includes the followingembodiments:

-   -   agricultural and veterinary compositions comprising an amount of        at least one compound of the formula (I) or a stereoisomer,        tautomer or salt thereof;    -   the use of the compounds of formula (I), the stereoisomers, the        tautomers or the salts thereof for combating invertebrate pests;    -   the use of the compounds of formula (I), the stereoisomers, the        tautomers or the salts thereof for protecting growing plants        from attack or infestation by invertebrate pests;    -   the use of the compounds of formula (I), the stereoisomers, the        tautomers or the salts, thereof for protecting plant        proparagation material, especially seeds, from soil insects;    -   the use of the compounds of formula (I), the stereoisomers, the        tautomers or the salts thereof for protecting the seedlings        roots and shoots of plants from soil and foliar insects;    -   a method for combating or controlling invertebrate pests, which        method comprises contacting said pest or its food supply,        habitat or breeding grounds with a pesticidally effective amount        of at least one compound of the formula (I) or a stereoisomer, a        tautomer or salt thereof;    -   a method for protecting growing plants from attack or        infestation by invertebrate pests, which method comprises        contacting a plant, or soil or water in which the plant is        growing, with a pesticidally effective amount of at least one        compound of the formula (I) or a stereoisomer, a tautomer or        salt thereof, in particular a method protecting crop plants from        attack or infestation by animal pests, which comprises        contacting the crop plants with a pesticidally effective amount        of at least one compound of the formula (I) or stereoisomer, a        tautomer or salt thereof;    -   a method for the protection of plant propagation, especially        seeds, from soil insects and of the seedlings' roots and shoots        from soil and foliar insects comprising contacting the seeds        before sowing and/or after pregermination with at least one        compound of the formula (I) or stereoisomer, a tautomer or salt        thereof;    -   seeds comprising a compound of the formula (I) or an enantiomer,        diastereomer or salt thereof;    -   the use of compounds of formula (I), the stereoisomers, the        tautomers or the salts, in particular the veterinary acceptable        salts, thereof for combating parasites in and on animals, in        particular for the use in the treatment of animals infested or        infected by parasites, for preventing animals of getting        infected or infested by parasites or for protecting animals        against infestation or infection by parasites;    -   a method for treating animals infested or infected by parasites        or preventing animals of getting infected or infested by        parasites or protecting animals against infestation or infection        by parasites which comprises administering or applying to the        animals a parasiticidally effective amount of a compound of        formula (I) or the stereoisomers and/or salts, in particular        veterinary acceptable salts, thereof;    -   a process for the preparation of a veterinary composition for        treating, controlling, preventing or protecting animals against        infestation or infection by parasites which comprises        formulating a compound of formula (I) or a stereoisomer,        tautomer and/or veterinary acceptable salt thereof with a        carrier composition suitable for veterinary use;    -   the use of a compound of formula (I) or the stereoisomers,        tautomers and/or veterinary acceptable salt thereof for the        preparation of a medicament for treating, controlling,        preventing or protecting animals against infestation or        infection by parasites.

The present invention also relates to plant propagation materials, inparticular as mentioned above to seeds, containing at least one compoundof formula (I), a stereoisomer, a tautomer and/or an agriculturallyacceptable salt thereof.

DETAILED DESCRIPTION OF INVENTION

The present invention relates to every possible stereoisomer of thecompounds of formula (I), i.e. to single enantiomers, diastereomers andE/Z-isomers as well as to mixtures thereof and also to the saltsthereof. The present invention relates to each isomer alone, or mixturesor combinations of the isomers in any proportion to each other.Depending on the substitution pattern, the compounds of the formula (I)may have one or more centers of chirality, in which case they arepresent as mixtures of enantiomers or diastereomers. One center ofchirality is the carbon ring atom carrying radical R¹. Another centre ofchirality may be the carbon atom which carries R³, in particular if R³is different from CN and the group [CR^(4a)R^(4b)]_(m)R⁵. The inventionprovides both the pure enantiomers or diastereomers and their mixturesand the use according to the invention of the pure enantiomers ordiastereomers of the compound I or its mixtures. Suitable compounds ofthe formula (I) also include all possible geometrical stereoisomers(cis/trans isomers) and mixtures thereof.

The present invention also relates to potential tautomers of thecompounds of formula (I) and also to the salts of such tautomers. Thepresent invention relates to the tautomer as such as well as to mixturesor combinations of the tautomers in any proportion to each other. Theterm “tautomers” encompasses isomers, which are derived from thecompounds of formula (I) by the shift of an H-atom involving at leastone H-atom located at a nitrogen, oxygen or sulphur atom. Examples oftautomeric forms are keto-enol forms, imine-enamine forms, urea-isoureaforms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.

The compounds of the present invention, i.e. the compounds of formula(I), their stereoisomers, their tautomers as well as their salts, inparticular their agriculturally acceptable salts and their veterinarilyacceptable salts, may be amorphous or may exist in one ore moredifferent crystalline states (polymorphs) or modifications which mayhave a different macroscopic properties such as stability or showdifferent biological properties such as activities. The presentinvention includes both amorphous and crystalline compounds of theformula (I), mixtures of different crystalline states or modificationsof the respective stereoisomers or tautomers, as well as amorphous orcrystalline salts thereof.

Salts of the compounds of the formula (I) are preferably agriculturallysalts as well as veterinarily acceptable salts. They can be formed in acustomary method, e.g. by reacting the compound with an acid of theanion in question if the compound of formula (I) has a basicfunctionality or by reacting an acidic compound of formula (I) with asuitable base.

Suitable agriculturally or veterinary useful salts are especially thesalts of those cations or anions, in particular the acid addition saltsof those acids, whose cations and anions, respectively, do not have anyadverse effect on the action of the compounds according to the presentinvention. Suitable cations are in particular the ions of the alkalimetals, preferably lithium, sodium and potassium, of the alkaline earthmetals, preferably calcium, magnesium and barium, and of the transitionmetals, preferably manganese, copper, zinc and iron, and also ammonium(NH₄ ⁺) and substituted ammonium in which one to four of the hydrogenatoms are replaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl orbenzyl. Examples of substituted ammonium ions comprise methylammonium,isopropylammonium, dimethylammonium, diisopropylammonium,trimethylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethylammonium,2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium,benzyltrimethylammonium and benzyltriethylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, phosphate, nitrate, hydrogen carbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting the compounds of the formulae Iwith an acid of the corresponding anion, preferably of hydrochloricacid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The organic moieties mentioned in the above definitions of the variablesare—like the term halogen—collective terms for individual listings ofthe individual group members. The prefix C_(n)-C_(m) indicates in eachcase the possible number of carbon atoms in the group.

“Halogen” will be taken to mean fluoro, chloro, bromo and iodo.

The term “partially or fully halogenated” will be taken to mean that 1or more, e.g. 1, 2, 3, 4 or 5 or all of the hydrogen atoms of a givenradical have been replaced by a halogen atom, in particular by fluorineor chlorine. For example, partially or fully halogenated alkyl is alsotermed haloalkyl, partially or fully halogenated cycloalkyl is alsotermed halocycloalkyl, partially or fully halogenated alkylenyl is alsotermed haloalkenyl, partially or fully halogenated alkylynyl is alsotermed haloalkynyl, partially or fully halogenated alkoxy is also termedhaloalkoxy, partially or fully halogenated alkylthio is also termedhaloalkthio, partially or fully halogenated alkylsulfinyl is also termedhaloalkylsulfinyl, partially or fully halogenated alkylsulfonyl is alsotermed haloalsulfonyl, partially or fully halogenated cycloalkylalkyl isalso termed halocycloalkylalkyl.

The term “C₁-C_(m)-alkyl” as used herein, and also inC₁-C_(m)-alkylamino, di-C₁-C_(m)-alkylamino,C₁-C_(m)-alkylaminocarbonyl, di-(C_(n)-C_(m)-alkylamino)carbonyl,C₁-C_(m)-alkylthio, C₁-C_(m)-alkylsulfinyl and C₁-C_(m)-alkylsulfonyl,refers to a branched or unbranched saturated hydrocarbon group having nto m, e.g. 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, forexample methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl,1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl,heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers.C₁-C₄-alkyl means for example methyl, ethyl, propyl, 1-methylethyl,butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl.

The term “C₁-C_(m)-haloalkyl” as used herein, and also inC₁-C_(m)-haloalkylthio (═C₁-C_(m)-haloalkylsulfenyl),C₁-C_(m)-haloalkylsulfinyl and C₁-C_(m)-haloalkylsulfonyl, refers to astraight-chain or branched alkyl group having n to m carbon atoms, e.g.1 to 10 in particular 1 to 6 carbon atoms (as mentioned above), wheresome or all of the hydrogen atoms in these groups may be replaced byhalogen atoms as mentioned above, for example C₁-C₄-haloalkyl, such aschloromethyl, bromomethyl, dichloromethyl, trichloromethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl andthe like. The term C₁-C₁₀-haloalkyl in particular comprisesC₁-C₂-fluoroalkyl, which is synonym with methyl or ethyl, wherein 1, 2,3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such asfluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl andpentafluoromethyl. “Halomethyl” is methyl in which 1, 2 or 3 of thehydrogen atoms are replaced by halogen atoms. Examples are bromomethyl,chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl,difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl and the like.

Similarly, “C₁-C_(m)-alkoxy”, “C₁-C_(m)-alkylthio”, or“C₁-C_(m)-alkylsulfenyl”, respectively, “C₁-C_(m)-alkylsulfinyl” or“C₁-C_(m)-alkylsulfonyl” refer to straight-chain or branched alkylgroups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or1 to 4 carbon atoms (as mentioned above) bonded through O, S, S(═O) orS(═O)₂ linkages, respectively, at any bond in the alkyl group.Accordingly, the terms “C₁-C_(m)-haloalkoxy”, “C₁-C_(m)-haloalkylthio”or “C₁-C_(m)-alkylsulfenyl”, respectively, “C₁-C_(m)-haloalkylsulfinyl”or “C₁-C_(m)-haloalkylsulfonyl”, refer to straight-chain or branchedalkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through O, S,S(═O) or S(═O)₂ linkages, respectively, at any bond in the haloalkylgroup, where some or all of the hydrogen atoms in these groups may bereplaced by halogen atoms as mentioned above.

The term “C₁-C_(m)-alkoxy” is a C₁-C_(m)-alkyl group, as defined above,attached via an oxygen atom. C₁-C₂-Alkoxy is methoxy or ethoxy.C₁-C₄-Alkoxy is, for example, methoxy, ethoxy, n-propoxy, 1-methylethoxy(isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy(isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). C₁-C₆-Alkoxy includesthe meanings given for C₁-C₄-alkoxy and also includes, for example,pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy,1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy,3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyor 1-ethyl-2-methylpropoxy. C₁-C₈-Alkoxy includes the meanings given forC₁-C₆-alkoxy and also includes, for example, heptyloxy, octyloxy,2-ethylhexyloxy and positional isomers thereof. C₁-C₁₀-Alkoxy includesthe meanings given for C₁-C₈-alkoxy and also includes, for example,nonyloxy, decyloxy and positional isomers thereof.

The term “C₁-C_(m)-alkylthio” is a C₁-C_(m)-alkyl group, as definedabove, attached via an oxygen atom. C₁-C₂-Alkylthio is methylthio orethylthio. C₁-C₄-Alkylthio is, for example, methylthio, ethylthio,n-propylthio, 1-methylethylthio (isopropylthio), butylthio,1-methylpropylthio (secbutylthio), 2-methylpropylthio (isobutylthio) or1,1-dimethylethylthio (tert-butylthio). C₁-C₆-Alkylthio includes themeanings given for C₁-C₄-alkylthio and also includes, for example,pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio,1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio,3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio,2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio,2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio.C₁-C₈-Alkylthio includes the meanings given for C₁-C₆-alkylthio and alsoincludes, for example, heptylthio, octylthio, 2-ethylhexylthio andpositional isomers thereof. C₁-C₁₀-Alkylthio includes the meanings givenfor C₁-C₈-alkylthio and also includes, for example, nonylthio, decylthioand positional isomers thereof.

The term “C₁-C_(m)-alkylsulfinyl” is a C₁-C_(m)-alkyl group, as definedabove, attached via a S(═O) group. The term “C₁-C_(m)-alkylsulfonyl” isa C₁-C_(m)-alkyl group, as defined above, attached via a S(═O)₂ group.

The term “C₁-C_(m)-haloalkyloxy” is a C₁-C_(m)-haloalkyl group, asdefined above, attached via an oxygen atom. Examples includeC₁-C₂-haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy,trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy,chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy,1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy,2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy and pentafluoroethoxy.

The term “C₁-C_(m)-haloalkylthio” is a C₁-C_(m)-haloalkyl group, asdefined above, attached via a sulfur atom. Examples includeC₁-C₂-haloalkylthio, such as chloromethylthio, bromomethylthio,dichloromethylthio, trichloromethylthio, fluoromethylthio,difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio,dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio,1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio andpentafluoroethylthio and the like.

Similarly the terms C₁-C₂-fluoroalkoxy and C₁-C₂-fluoroalkylthio referto C₁-C₂-fluoroalkyl which is bound to the remainder of the molecule viaan oxygen atom or a sulfur atom, respectively.

The term “C₁-C_(m)-haloalkylsulfinyl” is a C₁-C_(m)-haloalkyl group, asdefined above, attached via a S(═O) group. The term“C₁-C_(m)-haloalkylsulfonyl” is a C₁-C_(m)-haloalkyl group, as definedabove, attached via a S(═O)₂ group.

The term “C₂-C_(m)-alkenyl” as used herein denotes a linear or branchedethylenically unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10or 2 to 6 carbon atoms and a C═C-double bond in any position, such asethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term “C₂-C_(m)-haloalkenyl” as used herein, which is also expressedas “C₂-C_(m)-alkenyl which is partially or fully halogenated”, refers toC₂-C_(m)-alkenyl, where some or all of the hydrogen atoms in thesegroups are replaced by halogen atoms as mentioned above, in particularfluorine, chlorine and bromine, for example 1-fluoroethenyl,2-fluoroethenyl, 2,2-difluoroethenyl, 1,2,2-trifluoroethenyl,1-fluoro-2-propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl,1-fluoro-1-propenyl, 1,2-difluoro-1-propenyl, 3,3-difluoropropen-2-yl,1-chloroethenyl, 2-chloroethenyl, 2,2-dichloroethenyl,1-chloro-2-propenyl, and the like.

The term “C₂-C_(m)-alkynyl” as used herein refers to a linear orbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2to 6 carbon atoms and containing at least one triple bond, such asethynyl, propynyl, 1-butynyl, 2-butynyl, and the like.

The term “C₂-C_(m)-haloalkynyl” as used herein, which is also expressedas “C₂-C_(m)-alkynyl which is partially or fully halogenated”, refers toC₂-C_(m)-alkynyl, where some or all of the hydrogen atoms in thesegroups are replaced by halogen atoms as mentioned above, in particularfluorine, chlorine and bromine. Examples of C₂-C_(m)-haloalkynyl include1-fluoro-2-propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl,1-fluoro-2-propynyl and 1,1-difluoro-2-propenyl, and the like.

The term “C₃-C_(m)-cycloalkyl” as used herein refers to a monocyclic andpolycyclic 3- to m-membered saturated cycloaliphatic radicals, e.g.cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, cyclodecyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl,bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the termcycloalkyl denotes a monocyclic saturated hydrocarbon radical.

The term “C₃-C_(m)-halocycloalkyl” as used herein, which is alsoexpressed as “cycloalkyl which is partially or fully halogenated”,refers C₃-C_(m)-cycloalkyl as mentioned above, in which some or all ofthe hydrogen atoms are replaced by halogen atoms as mentioned above, inparticular fluorine, chlorine and bromine. Examples ofC₃-C_(m)-halocycloalkyl include 1-fluorocyclopropyl,2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 1-chlorocyclopropyl,2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,3-difluorocyclopropyl,1-fluorocyclobutyl etc.

The term “C₃-C_(m)-cycloalkyl-C₁-C₄-alkyl” refers to aC₃-C_(m)-cycloalkyl group as defined above, which is bound to theremainder of the molecule via a C₁-C₄-alkyl group, as defined above.Examples for C₃-C_(m)-cycloalkyl-C₁-C₄-alkyl are cyclopropylmethyl,cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl,cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl,cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl andcyclohexylpropyl.

The term “C₃-C_(m)-halocycloalkyl-C₁-C₄-alkyl” refers to aC₃-C_(m)-halocycloalkyl group as defined above which is bound to theremainder of the molecule via a C₁-C₄-alkyl group, as defined above.

The term “C₁-C₄-alkoxy-C₁-C₄-alkyl” as used herein refers to alkylhaving 1 to 4 carbon atoms, e.g. like specific examples mentioned above,wherein one hydrogen atom of the alkyl radical is replaced by anC₁-C₄-alkoxy group. Examples are methoxymethyl, ethoxymethyl,propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl,isobutoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl,1-propoxyethyl, 1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl,1-isobutoxyethyl, 1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl,2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl,2-isobutoxyethyl, 2-tert-butoxyethyl, 1-methoxypropyl, 1-ethoxypropyl,1-propoxypropyl, 1-isopropoxypropyl, 1-n-butoxypropyl,1-sec-butoxypropyl, 1-isobutoxypropyl, 1-tert-butoxypropyl,2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl,2-n-butoxypropyl, 2-sec-butoxypropyl, 2-isobutoxypropyl,2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl,3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl,3-isobutoxypropyl, 3-tert-butoxypropyl and the like.

The term C₁-C₄-haloalkoxy-C₁-C₄-alkyl is a straight-chain or branchedalkyl group having from 1 to 4 carbon atoms, wherein one of the hydrogenatoms is replaced by a C₁-C₄-alkoxy group and wherein at least one, e.g.1, 2, 3, 4 or all of the remaining hydrogen atoms, either in the alkoxymoiety or in the alkyl moiety or in both, are replaced by halogen atoms.Examples are difluoromethoxymethyl (CHF₂OCH₂), trifluoromethoxymethyl,1-difluoromethoxyethyl, 1-trifluoromethoxyethyl, 2-difluoromethoxyethyl,2-trifluoromethoxyethyl, difluoro-methoxy-methyl (CH₃OCF₂),1,1-difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.

The term “C₁-C_(m)-alkoxycarbonyl” is a C₁-C_(m)-alkoxy group, asdefined above, attached via an carbonyl group atom. C₁-C₂-Alkoxycarbonylis methoxycarbonyl or ethoxycarbonyl. C₁-C₄-Alkoxy is, for example,methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl,1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl,2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl.C₁-C₆-Alkoxycarbonyl includes the meanings given forC₁-C₄-alkoxycarbonyl and also includes, for example, pentoxycarbonyl,1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl,1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl,1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxy,2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl,1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or1-ethyl-2-methylpropoxycarbonyl.

The term “cycloalkenyl” as used herein refers to monocyclic hydrocarbonradicals with at least one C═C double bond in the ring, which ring ishowever not aromatic, the hydrocarbon radicals having 3 to 8(“C₃-C₈-cycloalkyl) carbon atoms. Examples are cyclopropenyl, such ascycloprop-1-enyl and cycloprop-2-yl, cyclobutenyl, such ascyclobut-1-enyl and cyclobut-2-enyl, cyclopentenyl, such ascyclopent-1-enyl, cyclopent-2-enyl and cyclopent-3-enyl,cyclopentadienyl, such as cyclopenta-1,3-dienyl, cyclopenta-1,4-dienyland cyclopenta-2,4-dienyl, cyclohexenyl, such as cyclohex-1-enyl,cyclohex-2-enyl and cyclohex-3-enyl, cyclohexadienyl, such ascyclohexa-1,3-dienyl, cyclohexa-1,4-dienyl, cyclohexa-1,5-dienyl andcyclohexa-2,5-dienyl, cycloheptenyl, cycloheptadienyl, cycloheptatrienylcyclooctenyl, cyclooctadieny, cyclooctatrienyl and cyclooctatetraenyl.

The term “aryl” as used herein refers to an aromatic hydrocarbon radicalsuch as naphthyl or in particular phenyl.

The term “3- to 6-membered carbocyclic ring” as used herein refers tocyclopropane, cyclobutane, cyclopentane and cyclohexane rings. The term“3- to 7-membered carbocyclic ring” as used herein refers tocyclopropane, cyclobutane, cyclopentane, cyclohexane and cycloheptanerings.

The term “3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturatedor aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms” or“containing heteroatom groups”, wherein those heteroatom(s) (group(s))are selected from N, O, S, NO, SO and SO₂ and are ring members, as usedherein refers to monocyclic radicals, the monocyclic radicals beingsaturated, partially unsaturated or aromatic. The heterocyclic radicalmay be attached to the remainder of the molecule via a carbon ringmember or via a nitrogen ring member.

Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ringsinclude: oxiranyl, aziridinyl, azetidinyl, 2 tetrahydrofuranyl,3-tetrahydrofuranyl, 2 tetrahydrothienyl, 3 tetrahydrothienyl,2-pyrrolidinyl, 3-pyrrolidinyl, 3 pyrazolidinyl, 4 pyrazolidinyl,5-pyrazolidinyl, 2 imidazolidinyl, 4 imidazolidinyl, 2-oxazolidinyl,4-oxazolidinyl, 5 oxazolidinyl, 3-isoxazolidinyl, 4 isoxazolidinyl, 5isoxazolidinyl, 2 thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3isothiazolidinyl, 4-isothiazolidinyl, 5 isothiazolidinyl,1,2,4-oxadiazolidin-3-yl, 1,2,4 oxadiazolidin 5 yl,1,2,4-thiadiazolidin-3-yl, 1,2,4 thiadiazolidin-5-yl, 1,2,4triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4 thiadiazolidin-2-yl,1,3,4 triazolidin-2-yl, 2-tetrahydropyranyl, 4 tetrahydropyranyl,1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2-piperidinyl, 3-piperidinyl,4-piperidinyl, 3-hexahydropyridazinyl, 4 hexahydropyridazinyl,2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5 hexahydropyrimidinyl,2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4hexahydrotriazin-3-yl, 2-morpholinyl, 3-morpholinyl, 2-thiomorpholinyl,3-thiomorpholinyl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl,1,1-dioxothiomorpholin-2-yl, 1,1-dioxothiomorpholin-3-yl,hexahydroazepin-1-, -2-, -3- or -4-yl, hexahydrooxepinyl,hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl,hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl,hexahydro-1,3-dioxepinyl, hexahydro-1,4-dioxepinyl and the like.Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturatedheterocyclic rings include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3dihydrothien-3-yl, 2,4 dihydrothien-2-yl, 2,4-dihydrothien-3-yl,2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3 pyrrolin-2-yl, 3-pyrrolin-3-yl,2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4 isoxazolin 3 yl,2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,2-isothiazolin-3-yl, 3 isothiazolin-3-yl, 4-isothiazolin-3-yl,2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4 isothiazolin-4-yl,2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl,2,3 dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl,3,4-dihydropyrazol-1-yl, 3,4 dihydropyrazol-3-yl,3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5 dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3 dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4 dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4 dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- ortetrahydropyridazinyl, 4 di- or tetrahydropyridazinyl, 2-di- ortetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5 di- ortetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- ortetrahydrotriazin-2-yl, 1,2,4-di- or tetrahydrotriazin-3-yl,2,3,4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1H]oxepin-2-, -3-, -4-,-5-, -6- or -7-yl, 2,3,4,7 tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6-or -7-yl, 2,3,6,7 tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl,tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl,tetrahydro-1,3-oxazepinyl, tetrahydro-1,4-oxazepinyl,tetrahydro-1,3-dioxepinyl and tetrahydro-1,4-dioxepinyl.

Examples of 5- or 6-membered aromatic heterocyclic rings, also termedheteroaromatic rings or hetaryl, include: 2-furyl, 3-furyl, 2-thienyl,3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl,5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-2-yl,2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.

A “C₂-C_(m)-alkylene” is divalent branched or preferably non-branched orlinear saturated aliphatic chain having 2 to m, e.g. 2 to 7 carbonatoms, for example CH₂CH₂, —CH(CH₃)—, CH₂CH₂CH₂, CH(CH₃)CH₂, CH₂CH(CH₃),CH₂CH₂CH₂CH₂, CH₂CH₂CH₂CH₂CH₂, CH₂CH₂CH₂CH₂CH₂CH₂, andCH₂CH₂CH₂CH₂CH₂CH₂CH₂.

Embodiments of the present invention as well preferred compounds of thepresent invention are outlined in the following paragraphs. The remarksmade below concerning preferred embodiments of the variables of thecompounds of formula (I), especially with respect to their substituentsX, W¹, W², W³, W⁴, Het, R¹, R², R³, R^(4a), R^(4b) and R⁵ and theirvariable k and m are valid both on their own and, in particular, inevery possible combination with each other.

When # appears in a formula showing a preferred substructure of acompound of the present invention, it denotes the attachment bond in theremainder molecule.

Preferred are compounds of formula (I), wherein Het is selected from thegroup consisting of radicals of formulae Het-1 to Het-24, withpreference given to compounds of the formula (I), their stereoisomers,there tautomers and their salts, where Het is selected from the radicalsof the formulae Het-1, Het-11 and Het-24:

wherein # denotes the bond to the remainder of the molecule in formula(I), and wherein R⁶ and k are as defined above and where R^(6a) ishydrogen or has one of the meanings given for R⁶ and where R^(6b) ishydrogen or a C-bound radical mentioned as R⁶ and where R^(6b) is inparticular hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl. In particular k is0, 1 or 2, especially 0 or 1. In formulae Het-1, Het-2, Het-3, Het-4,Het-7, Het-8, Het-9, Het-10, Het-11, Het-18 and Het-21, k isespecially 1. In particular R^(6a) in formulae Het-12, Het-13, Het-14,Het-16, Het-17, Het-19, Het 20 and Het-22 is different from hydrogen.

Irrespectively of its occurrence, R⁶ is preferably selected from thegroup consisting of halogen, cyano, C₁-C₆-alkyl, C₃-C₈-cycloalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may optionally bepartly or completely halogenated, in particular by fluorine or chlorine,or may further substituted independently from one another with one ormore R⁷, or R⁶ may also be a radical selected from the group consistingof OR⁸, NR^(17a)R^(17b), S(O)_(n)R⁸, S(O)_(n)NR^(17a)R^(17b),C(═O)R^(7a), C(═O)NR^(17a)R^(17b), C(═O)OR⁸, C(═S)R^(7a),C(═S)NR^(17a)R^(17b), C(═NR¹⁷)R^(7a), C(═NR¹⁷)NR^(17a)R^(17b).Irrespectively of its occurrence, R⁶ is in particular selected from thegroup consisting of halogen, such as chlorine or fluorine, C₁-C₄-alkyl,such as methyl or ethyl, C₁-C₄-alkoxy, such as methoxy or ethoxy,C₁-C₄-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, andC₁-C₄-haloalkyl, such as difluoromethyl, trifluoromethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, morepreferably from halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl, even morepreferably from fluorine, chlorine, C₁-C₂-alkyl, such as methyl or ethyland C₁-C₂-haloalkyl such as difluoromethyl, trifluoromethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.

Irrespectively of its occurrence, R^(6a) is preferably selected from thegroup consisting of hydrogen, halogen, cyano, C₁-C₆-alkyl,C₃-C₈-cycloalkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl, wherein the carbonatoms of the aforementioned aliphatic and cycloaliphatic radicals mayoptionally be partly or completely halogenated, in particular byfluorine or chlorine, or may further substituted independently from oneanother with one or more R⁷, or R^(6a) may also be a radical selectedfrom the group consisting of OR⁸, NR^(17a)R^(17b), S(O)_(n)R⁸,S(O)_(n)NR^(17a)R^(17b), C(═O)R^(7a), C(═O)NR^(17a)R^(17b), C(═O)OR⁸,C(═S)R^(7a), C(═S)NR^(17a)R^(17b), C(═NR¹⁷)R^(7a),C(═NR¹⁷)NR^(17a)R^(17b). Irrespectively of its occurrence, R^(6a) is inparticular selected from the group consisting of hydrogen, halogen, suchas chlorine or fluorine, C₁-C₄-alkyl, such as methyl or ethyl,C₁-C₄-alkoxy, such as methoxy or ethoxy, C₁-C₄-haloalkoxy, such asdifluoromethoxy or trifluoromethoxy, and C₁-C₄-haloalkyl, such asdifluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethylor pentafluoroethyl, more preferably from halogen, C₁-C₄-alkyl andC₁-C₄-haloalkyl, even more preferably from fluorine, chlorine,C₁-C₂-alkyl, such as methyl or ethyl and C₁-C₂-haloalkyl such asdifluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethylor pentafluoroethyl.

Irrespectively of its occurrence, R^(6b) is in particular selected fromthe group consisting of hydrogen, C₁-C₄-alkyl, such as methyl or ethyl,and C₁-C₄-haloalkyl, such as difluoromethyl, trifluoromethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, morepreferably C₁-C₂-alkyl, such as methyl or ethyl and C₁-C₂-haloalkyl suchas difluoromethyl, trifluoromethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl or pentafluoroethyl.

Particularly preferred are compounds of formula (I), wherein Het isselected from the group consisting of radicals of formulae Het-1,Het-11a and Het-24,

-   -   where    -   R⁶ is selected from the group consisting of halogen, such as        chlorine or fluorine, C₁-C₄-alkyl, such as methyl or ethyl,        C₁-C₄-alkoxy, such as methoxy or ethoxy, C₁-C₄-haloalkoxy, such        as difluoromethoxy or trifluoromethoxy, and C₁-C₄-haloalkyl,        such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl,        2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from        halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl, even more preferably        from fluorine, chlorine, C₁-C₂-alkyl, such as methyl or ethyl        and C₁-C₂-haloalkyl such as difluoromethyl, trifluoromethyl,        2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl; and        where    -   R^(6a) is selected from the group consisting of hydrogen,        halogen, such as chlorine or fluorine, C₁-C₄-alkyl, such as        methyl or ethyl, C₁-C₄-alkoxy, such as methoxy or ethoxy,        C₁-C₄-haloalkoxy, such as difluoromethoxy or trifluoromethoxy,        and C₁-C₄-haloalkyl, such as difluoromethyl, trifluoromethyl,        2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl,        more preferably from halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl,        even more preferably from fluorine, chlorine, C₁-C₂-alkyl, such        as methyl or ethyl and C₁-C₂-haloalkyl such as difluoromethyl,        trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or        pentafluoroethyl and    -   k is 0, 1 or 2.

A particularly preferred group of embodiments relates to compounds offormula (I) to the stereoisomers, the tautomers and to the saltsthereof, wherein Het is a radical of formula Het-1, where k is 0, 1 or2, in particular 1 or 2 and especially 1 and where R⁶ is as definedabove and in particular selected from the group consisting of halogen,such as chlorine or fluorine, C₁-C₄-alkyl, such as methyl or ethyl,C₁-C₄-alkoxy, such as methoxy or ethoxy, C₁-C₄-haloalkoxy, such asdifluoromethoxy or trifluoromethoxy, and C₁-C₄-haloalkyl, such asdifluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethylor pentafluoroethyl, more preferably from halogen, C₁-C₄-alkyl andC₁-C₄-haloalkyl, even more preferably from fluorine, chlorine,C₁-C₂-alkyl, such as methyl or ethyl and C₁-C₂-haloalkyl such asdifluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethylor pentafluoroethyl. Amongst the compounds of this particular group ofembodiments, a particular sub-group of embodiments relates to compoundsof the formula (I), to the stereoisomers, the tautomers and to the saltsthereof, wherein Het is a radical of formula Het-1a

-   -   where    -   R⁶ is as defined above and in particular selected from the group        consisting of halogen, such as chlorine or fluorine,        C₁-C₄-alkyl, such as methyl or ethyl, and C₁-C₄-haloalkyl, such        as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl,        2,2,2-trifluoroethyl or pentafluoroethyl, and even more        preferably from fluorine, chlorine, C₁-C₂-alkyl, such as methyl        or ethyl and C₁-C₂-haloalkyl such as difluoromethyl,        trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or        pentafluoroethyl;    -   R^(6a) is as defined above and in particular selected from the        group consisting of hydrogen, halogen, such as chlorine or        fluorine and C₁-C₄-alkyl, such as methyl or ethyl, more        preferably is hydrogen.

A special embodiment of the radical Het-1a is 6-chloropyridin-3-yl, i.e.R^(6a) is hydrogen and R⁶ is chlorine. A further special embodiment ofthe radical Het-1a is 6-(trifluoromethyl)pyridin-3-yl, i.e. R^(6a) ishydrogen and R⁶ is trifluoromethyl.

Another particularly preferred group of embodiments relates to compoundsof formula (I) to the stereoisomers, the tautomers and to the saltsthereof, wherein Het is a radical of formula Het-11, where k is 0, 1 or2, in particular 0 or 1, and where Het is in particular a radical offormula Het-11a,

where R^(6a) is as defined above and wherein R^(6a) is in particularselected from the group consisting of hydrogen, halogen, such aschlorine or fluorine, C₁-C₄-alkyl, such as methyl or ethyl,C₁-C₄-alkoxy, such as methoxy or ethoxy, C₁-C₄-haloalkoxy, such asdifluoromethoxy or trifluoromethoxy, and C₁-C₄-haloalkyl, such asdifluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethylor pentafluoroethyl, more preferably from halogen, C₁-C₄-alkyl andC₁-C₄-haloalkyl, even more preferably from fluorine, chlorine,C₁-C₂-alkyl, such as methyl or ethyl and C₁-C₂-haloalkyl such asdifluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethylor pentafluoroethyl. A special embodiment of the radical Het-11a is2-chlorothiazol-5-yl, i.e. R^(6a) is chlorine.

Another particularly preferred group of embodiments relates to compoundsof formula (I) to the stereoisomers, the tautomers and to the saltsthereof, wherein Het is a radical of formula Het-24, where k is 0, 1 or2, in particular 0 or 1, and where R⁶, if present, is as defined aboveand in particular selected from the group consisting of halogen, such aschlorine or fluorine, C₁-C₄-alkyl, such as methyl or ethyl, andC₁-C₄-haloalkyl, such as difluoromethyl, trifluoromethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and evenmore preferably from fluorine, chlorine, C₁-C₂-alkyl, such as methyl orethyl and C₁-C₂-haloalkyl such as difluoromethyl, trifluoromethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.

Preferred are compounds of formula (I), wherein R¹ and R² areindependently from each other selected from the group consisting ofhydrogen, halogen, such as fluorine or chlorine, CN, C₁-C₆-alkyl, inparticular C₁-C₄-alkyl, such as methyl, ethyl, n-propyl or isopropyl,C₃-C₆-cycloalkyl, such as cyclopropyl or cyclobutyl, C₁-C₆-haloalkyl, inparticular C₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl,trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, or C₃-C₆-halocycloalkyl such as1-fluorocyclopropyl or 2,2-difluorocyclopropyl.

Preferred are also compounds of formula (I), wherein R¹ and R² maytogether be ═CR¹³R¹⁴.

Preferred are also compounds of formula (I), wherein R¹ and R² form,together with the carbon atom, which they attached to, a 3- to 5membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl orcyclopentyl.

Even more preferred are compounds of formula (I), wherein R¹ and R² areindependently from each other selected from the group consisting ofhydrogen, halogen, cyano, C₁-C₃-alkyl, such as methyl ethyl orisopropyl, or C₁-C₃-haloalkyl such as fluoromethyl, difluoromethyl,trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl.

Preferably at least one of the radicals R¹ and R² is hydrogen.

Especially more preferred are compounds of formula (I), wherein R¹ andR² are both hydrogen.

Especially more preferred are also compounds of formula (I), wherein oneof R¹ and R² is methyl while the other is hydrogen.

According to a first group of embodiments A, compounds of formula (I)are preferred, wherein R³ is selected from the group consisting ofhydrogen, halogen, CN, C₁-C₆-alkyl, in particular C₁-C₄-alkyl,C₁-C₆-haloalkyl, in particular C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, suchas cyclopropyl or cyclobutyl, C₃-C₆-halocycloalkyl, such as1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl,2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 1-fluorocyclobutyl,2-fluorocyclobutyl, 3-fluorocyclobutyl, 2,2-difluorocyclobutyl or3,3-difluorocyclobutyl, NR^(9a)R^(9b) and NR^(9a)—C(═O)R^(7a).

In the context of R³, the radicals R^(7a) is preferably selected fromthe group consisting of hydrogen, C₁-C₄-alkyl, such as methyl, ethyl,n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and C₁-C₄-haloalkyl,such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl. In the context of R³, the radicals R^(9a) andR^(9b) are preferably selected from the group consisting of hydrogen,C₁-C₄-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl,2-butyl or isobutyl, and C₁-C₄-haloalkyl, such as fluoromethyl,difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,2,2-difluoroethyl or 2,2,2-trifluoroethyl, or NR^(9a)R^(9b) may also bea saturated N-bound 3-, 4-, 5- or 6-membered heterocycle, which inaddition to the nitrogen atom may have 1 further heteroatom as ringmembers, which is selected from O and N and where the N-bound 3-, 4-, 5-or 6-membered heterocycle may be unsubstituted or carry 1, 2, 3 or 4radicals selected from C₁-C₄-alkyl and C₁-C₄-haloalkyl. Examples ofradicals NR^(9a)R^(9b) include, but are not limited to methylamino,ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino,isobutylamino, dimethylamino, diethylamino, di-n-propylamino,di-n-butylamino, N-methyl-N-ethylamino, N-methyl-N-propylamino,N-methyl-N-n-propylamino, N-methyl-N-isopropylamino,N-methyl-N-n-butylamino, N-methyl-N-2-butylamino,N-methyl-N-isobutylamino, 1-pyrrolidinyl, 1-piperidinyl, 1-piperazinyl,4-methyl-1-piperazinyl and 4-morpholinyl. Examples of radicalsNR^(9a)C(═O)R^(7a) include, but are not limited NH—C(═O)H, NH—C(═O)CH₃,NH—C(═O)CH₂CH₃ and NH—C(═O)CH(CH₃)₂.

In this group of embodiments A, the radical R³ is in particular selectedfrom the group consisting of hydrogen, fluorine, chlorine, C₁-C₄-alkyl,such as methyl, ethyl, n-propyl, isopropyl or n-butyl,NHC(═O)—C₁-C₄-alkyl, such as

NH—C(═O)H, NH—C(═O)CH₃, NH—C(═O)CH₂CH₃ or NH—C(═O)CH(CH₃)₂, and CN.

In this group of embodiments A, the radical R³ is especially selectedfrom the group consisting of hydrogen and C₁-C₄-alkyl, such as methyl,ethyl, n-propyl, isopropyl or n-butyl.

In this group of embodiments A, preference is given to compounds offormula (I), wherein R⁵ is selected from the group consisting ofhydrogen, halogen, CN, NR^(9a)R^(9b), C₁-C₆-alkyl, in particularC₁-C₄-alkyl, C₁-C₆-haloalkyl, in particular C₁-C₄-haloalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C(═O)OR⁸, C(═O)NR^(9a)R^(9b),C(═S)NR^(9a)R^(9b), C(═O)R^(7a), C(═S)R^(7a), Q-phenyl, where phenyl isunsubstituted or substituted with 1, 2, 3, 4 or 5 identical or differentsubstituents R¹⁰, or Q-Het^(#), where Het^(#) is unsubstituted orsubstituted with 1, 2, 3, 4 or 5 identical or different substituentsR¹⁰,

and where Q, irrespectively of its occurrence, is a bond, NR^(9a), suchas NH or N(CH₃) NR^(9a)—C(═O), such as NH—C(═O)H, NH—C(═O)CH₃,NH—C(═O)CH₂CH₃ or NH—C(═O)CH(CH₃)₂, OC(═O), NR^(9a)CH₂, such as NHCH₂ orN(CH₃)CH₂, OC(═O)CH₂, or NR^(9a)C(═O)CH₂ such as NHC(═O)CH₂.

In context of R⁵, Het^(#) is preferably 5- or 6-membered hetaryl such aspyridyl, thienyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, pyrazolyl,imidazolyl, oxazolyl or isoxazolyl, which is unsubstituted orsubstituted by 1, 2 or 3 radicals R¹⁰. In this context, R¹⁰ ispreferably selected from the group consisting of halogen, such aschlorine or fluorine, CN, C₁-C₄-alkyl, such as methyl, ethyl, n-propyland isopropyl, C₁-C₄-haloalkyl, in particular C₁-C₂-haloalkyl, such asfluoromethyl, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl,2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C₁-C₄-alkoxy,such as methoxy, ethoxy, n-propoxy and isopropoxy, and C₁-C₄-haloalkoxy,in particular C₁-C₂-haloalkoxy, such as fluoromethoxy, difluoromethoxy,trifluoromethoxy, 1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxyor 2,2,2-trifluoroethoxy.

In context of R⁵, the radical R^(7a) is preferably selected from thegroup consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, wherethe phenyl ring in the last two radicals is unsubstituted or substitutedby 1, 2 or 3 identical or different radicals selected from the groupconsisting of halogen, such as chlorine or fluorine, CN, C₁-C₄-alkyl,such as methyl, ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, inparticular C₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl,trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy. R^(7a) is in particular C₁-C₄-alkyl.

In context of R⁵, the radical R⁸ is preferably selected from the groupconsisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ringin the last two radicals is unsubstituted or substituted by 1, 2 or 3identical or different radicals selected from the group consisting ofhalogen, such as chlorine or fluorine, CN, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy. R⁸ is in particular C₁-C₄-alkyl.

In context of R⁵, the radicals R^(9a) and R^(9b) are preferably selectedfrom the group consisting of hydrogen, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, andC₁-C₄-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, or NR^(9a)R^(9b) may also be a saturated N-bound3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogenatom may have 1 further heteroatom as ring members, which is selectedfrom O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocyclemay be unsubstituted or carry 1, 2, 3 or 4 radicals selected fromC₁-C₄-alkyl and C₁-C₄-haloalkyl. Examples of such radicals NR^(9a)R^(9b)include, but are not limited to methylamino, ethylamino, n-propylamino,isopropylamino, n-butylamino, 2-butylamino, isobutylamino,dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino,N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino,N-methyl-N-isopropylamino, N-methyl-N-n-butylamino,N-methyl-N-2-butylamino, N-methyl-N-isobutylamino, 1-pyrrolidinyl,1-piperidinyl, 1-piperazinyl, 4-methyl-1-piperazinyl and 4-morpholinyl.

In context of R⁵, the radical R¹⁰ is preferably selected from the groupconsisting of halogen, such as chlorine or fluorine, CN, C₁-C₄-alkyl,such as methyl, ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, inparticular C₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl,trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy.

In this group of embodiments A, the radical R⁵ is in particular selectedfrom the group consisting of hydrogen, halogen, such as fluorine orchlorine, CN, C₁-C₆-alkyl, in particular C₁-C₄-alkyl, such as methyl,ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl,C₁-C₆-haloalkyl, in particular C₁-C₄-haloalkyl, such as fluoromethyl,difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,2,2-difluoroethyl or 2,2,2-trifluoroethyl, C₃-C₆-cycloalkyl, such ascyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,C₃-C₆-halocycloalkyl, such as 1-fluorocyclopropyl, 2-fluorocyclopropyl,2,2-difluorocyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl,1-fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl,2,2-difluorocyclobutyl or 3,3-difluorocyclobutyl, and phenyl, which isunsubstituted or carries 1, 2, 3, 4 or 5 identical or differentsubstituents R¹⁰.

The variable m is preferably 0, 1 or 2, in particular with regard to thegroup of embodiments A.

If R^(4a) and R^(4b) are present, i.e. if m is different from 0 and inparticular 1 or 2, and especially 1, the variables R^(4a) and R^(4b) arein particular selected, independently from one another, from the groupconsisting of hydrogen, C₁-C₄-alkyl, in particular methyl, and halogen,in particular fluorine or chlorine, or R^(4a) and R^(4b) together are═O.

According to a second group of embodiments B, compounds of formula (I)are preferred, wherein

-   R³ and R⁵ together with the carbon atom, to which they are bound,    form a 3, 4, 5 or 6 membered saturated carbocycle, in particular a    3-membered carbocycle, wherein the carbocycle may be unsubstituted    or may carry 1, 2, 3, 4, 5 or 6 radicals R^(7b), wherein R^(7b) is    as defined above and wherein    -   R^(7b) is in particular selected from the group consisting of        halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, and C₂-C₆-alkynyl, and        wherein the carbon atoms of the aforementioned aliphatic        radicals may optionally be partly or completely halogenated        and/or substituted by a radical selected from C₁-C₄-alkoxy,        C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyloxy,        C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-alkylsulfanyl,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, phenoxy, 5- or 6-membered        saturated heterocyclyl having 1 heteroatom selected from O and        S, such as tetrahydropyranyl, tetrahydrofuranyl and        tetrahydrothiopyranyl, where the 5- or 6-membered saturated        heterocyclyl may be unsubstituted or carry 1 or 2 radicals        selected from C₁-C₄-alkyl and C₁-C₄-alkoxy, and wherein one or        two radicals R^(7b) may also be        -   C₃-C₈-cycloalkyl, in particular C₃-C₆-cycloalkyl, which is            unsubstituted or carries 1, 2, 3, 4 or 5 radicals selected            from fluorine, chlorine, C₁-C₄-alkyl such as methyl and            C₁-C₄-alkoxycarbonyl such as methoxycarbonyl,        -   C₃-C₆-cycloalkenyl, which is unsubstituted or carries 1, 2,            3, 4 or 5 radicals selected from fluorine, chlorine or            C₁-C₄-alkyl such as methyl,        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different substituents R^(10b), or        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            such as tetrahydrofuryl, tetrahydropyranyl,            tetrahydrothiopyranyl or thiazolyl, where the heterocyclic            ring is optionally substituted with 1, 2, 3 or 4 identical            or different substituents R^(10b), and wherein the nitrogen            and/or the sulfur atom(s) of the heterocyclic ring may            optionally be oxidized, in particular a 5- or 6-membered            hetaryl having 1 or 2 heteroatoms selected from O, S and N,            where the 5- or 6-membered hetaryl is unsubstituted or            carries 1, 2 or 3 identical or different substituents            R^(10b),        -   or two of R^(7b) present on one ring carbon may together            form ═O or ═S,        -   or two R^(7b) together form a linear C₂-C₇ alkylene chain,            thus forming, together with the carbon atom to which they            are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or            2 CH₂ moieties of the alkylene chain may be replaced by 1 or            2 heteroatom moieties selected from O and S, and where the            alkylene chain is unsubstituted or may be substituted with            1, 2, 3, 4, 5 or 6 radicals selected from the group            consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, where    -   R^(10b) has one of the meanings give for R¹⁰ and where R^(10b)        is in particular selected from the group consisting of halogen,        CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy,    -   in particular, wherein-   R³ and R⁵ together with the carbon atom, to which they are bound,    form a 3, 4, 5 or 6 membered saturated carbocycle, in particular a    3-membered carbocycle, wherein the carbocycle may be unsubstituted    or may carry 1, 2, 3, 4, 5 or 6 radicals R^(7b), wherein R^(7b) is    as defined above and wherein    -   R^(7b) is in particular selected from the group consisting of        halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, and C₂-C₆-alkynyl, and        wherein the carbon atoms of the aforementioned aliphatic        radicals may optionally be partly or completely halogenated, and        wherein one or two radicals R^(7b) may also be        -   C₃-C₈-cycloalkyl, in particular C₃-C₆-cycloalkyl, which is            unsubstituted or carries 1, 2, 3, 4 or 5 radicals selected            from fluorine, chlorine or methyl,        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different substituents R^(10b), or        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            such as tetrahydrofuryl, tetrahydropyranyl,            tetrahydrothiopyranyl or thiazolyl, where the heterocyclic            ring is optionally substituted with 1, 2, 3 or 4 identical            or different substituents R^(10b), and wherein the nitrogen            and/or the sulfur atom(s) of the heterocyclic ring may            optionally be oxidized, in particular a 5- or 6-membered            hetaryl having 1 or 2 heteroatoms selected from O, S and N,            where the 5- or 6-membered hetaryl is unsubstituted or            carries 1, 2 or 3 identical or different substituents            R^(10b),        -   or two of R^(7b) present on one ring carbon may together            form ═O or ═S,        -   or two R^(7b) together form a linear C₂-C₇ alkylene chain,            thus forming, together with the carbon atom to which they            are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or            2 CH₂ moieties of the alkylene chain may be replaced by 1 or            2 heteroatom moieties selected from O and S, and where the            alkylene chain is unsubstituted or may be substituted with            1, 2, 3, 4, 5 or 6 radicals selected from the group            consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, where    -   R^(10b) has one of the meanings give for R¹⁰ and where R^(10b)        is in particular selected from the group consisting of halogen,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

According to the second group of embodiments B, particular preference isgiven to compounds of formula (I), wherein

-   R³ and R⁵ together with the carbon atom, to which they are bound,    form a 3 or 4 membered saturated carbocycle, i.e. a    1,1-cyclopropylidene or 1,1-cyclobutylidene radical, in particular a    1,1-cyclopropylidene radical wherein the carbocycle may be    unsubstituted or may carry 1, 2, 3, 4, 5 or 6 radicals R^(7b),    wherein    -   R^(7b) is as defined above and in particular selected from the        group consisting of halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl,        -   and wherein one radical R^(7b) may also be        -   C₃-C₆-cycloalkyl, which is unsubstituted or carries 1, 2, 3,            4 or 5 radicals selected from fluorine, chlorine,            C₁-C₄-alkyl such as methyl, or C₁-C₄-alkoxycarbonyl, or            phenyl, optionally substituted with 1, 2, 3, 4 or 5, in            particular 1, 2 or 3, identical or different substituents            R^(10b), where    -   R^(10b) is as defined above, and in particular selected from the        group consisting of halogen, such as fluorine or chlorine,        C₁-C₄-alkyl, CN, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy.

According to the second group of embodiments B, more preference is givento compounds of formula (I), wherein

-   R³ and R⁵ together with the carbon atom, to which they are bound,    form a 3 or 4 membered saturated carbocycle, i.e. a    1,1-cyclopropylidene or 1,1-cyclobutylidene radical, in particular a    1,1-cyclopropylidene radical wherein each of the carbon atoms of the    carbocycle may be unsubstituted or may carry 1, 2, 3, 4, 5 or 6    radicals R^(7b), wherein    -   R^(7b) is as defined above and in particular selected from the        group consisting of halogen, C₁-C₄-alkyl, and wherein one        radical R^(7b) may also be        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5, in            particular 1, 2 or 3, identical or different substituents            R^(10b), where    -   R^(10b) is as defined above, and in particular selected from the        group consisting of halogen, such as fluorine or chlorine,        C₁-C₄-alkyl, CN, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy.

According to the second group of embodiments B, even more particularpreference is given to compounds of formula (I), wherein R³ and R⁵together form the following moieties:

CH₂—CH₂, CHF—CH₂, CF₂—CH₂, CHF—CHF, CF₂—CHF, CF₂—CF₂, CHCl—CH₂,CCl₂—CH₂, CHCl—CHCl, CCl₂—CHCl, CCl₂—CCl₂, CH(CH₃)—CH₂, C(CH₃)₂—CH₂,CH(CH₃)—CH(CH₃), C(CH₃)₂—CH(CH₃), C(CH₃)₂—C(CH₃)₂, CH(OCH₃)—CH₂,CH(CH₂CH₃)—CH₂, CH(CH₂CH₂CH₃)—CH₂, CH(CH₂CH₂CH₂CH₃)—CH₂,CH(CH₃)—CH₂—CH₂, CH₂—CH(CH₃)—CH₂, C(CH₃)₂—CH₂—CH₂, CH₂—C(CH₃)₂—CH₂,CH(CH₃)—CH(CH₃)—CH₂, CH(CH₃)—CH₂—CH(CH₃), CH(CH₃)—CH(CH₃)—CH(CH₃),C(CH₃)₂—CH(CH₃)—CH₂, CH(CH₃)—C(CH₃)₂—CH₂, C(CH₃)₂—CH₂—C(CH₃)₂,C(CH₃)₂—C(CH₃)₂—CH₂, C(CH₃)₂—C(CH₃)₂—C(CH₃)₂, CHF—CH₂—CH₂, CH₂—CHF—CH₂,CF₂—CH₂—CH₂, CH₂—CF₂—CH₂, CHF—CHF—CH₂, CHF—CH₂—CHF, CHF—CHF—CHF,CF₂—CHF—CH₂, CHF—CF₂—CH₂, CF₂—CH₂—CF₂, CF₂—CF₂—CH₂, CF₂—CF₂—CF₂,CHCl—CH₂—CH₂, CH₂—CHCl—CH₂, CCl₂—CH₂—CH₂, CH₂—CCl₂—CH₂, CHCl—CHCl—CH₂,CHCl—CH₂—CHCl, CHCl—CHCl—CHCl, CCl₂—CHCl—CH₂, CHCl—CCl₂—CH₂,CCl₂—CH₂—CCl₂, CCl₂—CCl₂—CH₂, CCl₂—CCl₂—CCl₂,a radical CH(R^(7bb))—CH₂, where R^(7bb) is selected from the groupconsisting of

-   -   C₂-C₁₀-alkyl, such as ethyl, n-propyl, isopropyl, n-butyl,        tert.butyl, 1-methylpropyl, 2-methylpropyl, 1,2-dimethylpropyl,        2,2-dimethylpropyl, 3,3-dimethylpropyl, 1-methylbutyl,        1,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl, 1-ethylpentyl,    -   C₂-C₄-haloalkyl, such as 2,2-difluoroethyl, 1,1-difluoroethyl or        2,2,2-trifluoroethyl,    -   C₁-C₆-alkyl, which is substituted by 1 radical selected from        C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy,        C₁-C₄-alkylsulfanyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy,        phenoxy and 5- or 6-membered saturated heterocyclyl having 1        heteroatom selected from O and S, such as tetrahydropyranyl,        tetrahydrofuranyl, tetrahydrothiopyranyl, where        C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy and 5- or 6-membered        saturated heterocyclyl may be unsubstituted or carry 1 or 2        radicals selected from C₁-C₄-alkyl and C₁-C₄-alkoxy, examples of        substituted C₁-C₆-alkyl including 1-methoxyethyl,        2-methoxyethyl, 1-propoxyethyl, 2-propoxyethyl,        1-isopropoxyethyl, 2-isopropoxyethyl, 1-isobutoxyethyl,        2-isobutoxyethyl, 1-(cyclohexyloxy)ethyl, 2-phenoxyethyl,        (4-isopropylcyclohexyl)methyl, 1-acetoxyethyl, 2-acetoxyethyl,        6-acetoxyhexyl, 2-methylsulfanylpropyl,        1-methyl-2-methylsulfanylethyl, tetrahydropyran-4-ylmethyl,        tetrahydrothiopyran-4-ylmethyl,    -   C₂-C₁₀-alkenyl, such as 3-nonenyl,    -   C₃-C₁₀-cycloalkyl, optionally substituted by 1 or 2 C₁-C₄-alkyl,        such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,        cycloheptyl, cyclooctyl, 4-methylcyclohexyl,        4-isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl,    -   C₅-C₆-cycloalkenyl, optionally substituted by 1 or 2        C₁-C₄-alkyl, such as 2-methylcyclohex-3-en-1-yl,    -   5- or 6-membered saturated heterocyclyl having 1 heteroatom        selected from O and S, such as tetrahydropyranyl,        tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or        6-membered saturated heterocyclyl may be unsubstituted or carry        1 or 2 radicals selected from C₁-C₄-alkyl and C₁-C₄-alkoxy,        examples including tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,        tetrahydropyran-3-yl, tetrahydropyran-4-yl,        tehtrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl,        6-methoxy-3-methyltetrahydropyran-2-yl, and        5,5-dimethyltetrahydrofuran-2-yl,    -   optionally substituted phenyl such as phenyl, 2-chloropheynl,        2-fluoropheynl, 2-methylphenyl, 2-methoxyphenyl, 2-cyanophenyl,        3-chloropheynl, 3-fluoropheynl, 3-methylphenyl, 3-methoxyphenyl,        3-cyanophenyl, 4-chloropheynl, 4-fluoropheynl, 4-methylphenyl,        4-methoxyphenyl, 3-nitrophenyl, 4-(trifluoromethyl)phenyl,        3-(trifluoromethyl)phenyl and 4-cyanophenyl,    -   5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring        members, selected from O, S and N and where the hetaryl is        unsubstituted or substituted by 1 or 2 radicals selected from        halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy examples of hetaryl including        4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl,    -   phenyl-C₁-C₄-alkyl, such as benzyl or phenethyl, and    -   hetaryl-C₁-C₄-alkyl, where the hetaryl is 5- or 6-membered and        has 1 or 2 heteroatoms as ring members, selected from O, S and N        and where the hetaryl is unsubstituted or substituted by 1 or 2        radicals selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy and C₁-C₄-haloalkoxy examples of        hetaryl-C₁-C₄-alkyl including 1,1-dimethyl-2-(3-pyridyl)ethyl,        thereby forming, together with the carbon atom they are bound        to, an unsubstituted or substituted 1,1-cyclopropylidene or        1,1-cyclobutylidene radical.

According to the second group of embodiments B, even more particularpreference is given to compounds of formula (I), wherein R³ and R⁵together form the following moieties:

CH₂—CH₂, CHF—CH₂, CF₂—CH₂, CHF—CHF, CF₂—CHF, CF₂—CF₂, CHCl—CH₂,CCl₂—CH₂, CHCl—CHCl, CCl₂—CHCl, CCl₂—CCl₂, CH(CH₃)—CH₂, C(CH₃)₂—CH₂,CH(CH₃)—CH(CH₃), C(CH₃)₂—CH(CH₃), C(CH₃)₂—C(CH₃)₂, CH(OCH₃)—CH₂,CH(CH₂CH₃)—CH₂, CH(CH₂CH₂CH₃)—CH₂, CH(CH₂CH₂CH₂CH₃)—CH₂,CH(CH₃)—CH₂—CH₂, CH₂—CH(CH₃)—CH₂, C(CH₃)₂—CH₂—CH₂, CH₂—C(CH₃)₂—CH₂,CH(CH₃)—CH(CH₃)—CH₂, CH(CH₃)—CH₂—CH(CH₃), CH(CH₃)—CH(CH₃)—CH(CH₃),C(CH₃)₂—CH(CH₃)—CH₂, CH(CH₃)—C(CH₃)₂—CH₂, C(CH₃)₂—CH₂—C(CH₃)₂,C(CH₃)₂—C(CH₃)₂—CH₂, C(CH₃)₂—C(CH₃)₂—C(CH₃)₂, CHF—CH₂—CH₂, CH₂—CHF—CH₂,CF₂—CH₂—CH₂, CH₂—CF₂—CH₂, CHF—CHF—CH₂, CHF—CH₂—CHF, CHF—CHF—CHF,CF₂—CHF—CH₂, CHF—CF₂—CH₂, CF₂—CH₂—CF₂, CF₂—CF₂—CH₂, CF₂—CF₂—CF₂,CHCl—CH₂—CH₂, CH₂—CHCl—CH₂, CCl₂—CH₂—CH₂, CH₂—CCl₂—CH₂, CHCl—CHCl—CH₂,CHCl—CH₂—CHCl, CHCl—CHCl—CHCl, CCl₂—CHCl—CH₂, CHCl—CCl₂—CH₂,CCl₂—CH₂—CCl₂, CCl₂—CCl₂—CH₂, CCl₂—CCl₂—CCl₂ or a radical CH(Ar)—CH₂,where Ar is selected from phenyl, 2-chloropheynl, 2-fluoropheynl,2-methylphenyl, 2-methoxyphenyl, 2-cyanophenyl, 3-chloropheynl,3-fluoropheynl, 3-methylphenyl, 3-methoxyphenyl, 3-cyanophenyl,4-chlorophenyl, 4-fluoropheynl, 4-methylphenyl, 4-methoxyphenyl and4-cyanophenyl,thereby forming, together with the carbon atom they are bound to, anunsubstituted or substituted 1,1-cyclopropylidene or 1,1-cyclobutylideneradical.

According to the second group of embodiments B, special preference isgiven to compounds of formula (Ia) and (Ib),

where Het, W¹, W², W³, W⁴, X, R¹ and R² are as defined above and inparticular have the preferred meanings or the particularly preferredmeanings;

R^(7b1) is hydrogen or has one of the meanings given for R^(7b);

R^(7b2), R^(7b3) and R^(7b4) are hydrogen, methyl or halogen, inparticular hydrogen.

In formulae (Ia) and (Ib), R^(7b1) is in particular hydrogen or aradical selected from the group consisting of

-   -   C₁-C₁₀-alkyl, such as methyl, ethyl, n-propyl, isopropyl,        n-butyl, tert.butyl, 1-methylpropyl, 2-methylpropyl,        1,2-dimethylpropyl, 2,2-dimethylpropyl, 3,3-dimethylpropyl,        1-methylbutyl, 1,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl,        1-ethylpentyl,    -   C₁-C₄-haloalkyl, such as difluoromethyl, trifluoromethyl,        2,2-difluoroethyl, 1,1-difluoroethyl or 2,2,2-trifluoroethyl,    -   C₁-C₆-alkyl, which is substituted by 1 radical selected from        C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy,        C₁-C₄-alkylsulfanyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy,        phenoxy and 5- or 6-membered saturated heterocyclyl having 1        heteroatom selected from O and S, such as tetrahydropyranyl,        tetrahydrofuranyl, tetrahydrothiopyranyl, where        C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy and 5- or 6-membered        saturated heterocyclyl may be unsubstituted or carry 1 or 2        radicals selected from C₁-C₄-alkyl and C₁-C₄-alkoxy, examples of        substituted C₁-C₆-alkyl including 1-methoxyethyl,        2-methoxyethyl, 1-propoxyethyl, 2-propoxyethyl,        1-isopropoxyethyl, 2-isopropoxyethyl, 1-isobutoxyethyl,        2-isobutoxyethyl, 1-(cyclohexyloxy)ethyl, 2-phenoxyethyl,        (4-isopropylcyclohexyl)methyl, 1-acetoxyethyl, 2-acetoxyethyl,        6-acetoxyhexyl, 2-methylsulfanylpropyl,        1-methyl-2-methylsulfanylethyl, tetrahydropyran-4-ylmethyl,        tetrahydrothiopyran-4-ylmethyl,    -   C₂-C₁₀-alkenyl, such as 3-nonenyl,    -   C₃-C₁₀-cycloalkyl, optionally substituted by 1 or 2 C₁-C₄-alkyl,        such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,        cycloheptyl, cyclooctyl, 4-methylcyclohexyl,        4-isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl,    -   C₅-C₆-cycloalkenyl, optionally substituted by 1 or 2        C₁-C₄-alkyl, such as 2-methylcyclohex-3-en-1-yl,    -   5- or 6-membered saturated heterocyclyl having 1 heteroatom        selected from O and S, such as tetrahydropyranyl,        tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or        6-membered saturated heterocyclyl may be unsubstituted or carry        1 or 2 radicals selected from C₁-C₄-alkyl and C₁-C₄-alkoxy,        examples including tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,        tetrahydropyran-3-yl, tetrahydropyran-4-yl,        tehtrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl,        6-methoxy-3-methyltetrahydropyran-2-yl, and        5,5-dimethyltetrahydrofuran-2-yl,    -   optionally substituted phenyl such as phenyl, 2-chloropheynl,        2-fluoropheynl, 2-methylphenyl, 2-methoxyphenyl, 2-cyanophenyl,        3-chloropheynl, 3-fluoropheynl, 3-methylphenyl, 3-methoxyphenyl,        3-cyanophenyl, 4-chloropheynl, 4-fluoropheynl, 4-methylphenyl,        4-methoxyphenyl, 3-nitrophenyl, 4-(trifluoromethyl)phenyl,        3-(trifluoromethyl)phenyl and 4-cyanophenyl,    -   5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring        members, selected from O, S and N and where the hetaryl is        unsubstituted or substituted by 1 or 2 radicals selected from        halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy examples of hetaryl including        4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl,    -   phenyl-C₁-C₄-alkyl, such as benzyl or phenethyl, and    -   hetaryl-C₁-C₄-alkyl, where the hetaryl is 5- or 6-membered and        has 1 or 2 heteroatoms as ring members, selected from O, S and N        and where the hetaryl is unsubstituted or substituted by 1 or 2        radicals selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy and C₁-C₄-haloalkoxy examples of        hetaryl-C₁-C₄-alkyl including 1,1-dimethyl-2-(3-pyridyl)ethyl.

According to a third group of embodiments C, compounds of formula (I)are preferred, wherein R³ and R⁵ together with the carbon atom, to whichthey are bound, form a 3, 4, 5 or 6 membered saturated heterocyclehaving 1 or 2 non adjacent heteroatoms as ring members which areselected from O and S, wherein the heterocycle may be unsubstituted ormay carry 1, 2, 3, 4, 5 or 6 radicals R^(7b), wherein

-   -   R^(7b) is as defined above and in particular as defined for        embodiment B and especially selected from the group consisting        of halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl,        -   and wherein one radical R^(7b) may also be        -   C₃-C₆-cycloalkyl, which is unsubstituted or carries 1, 2, 3,            4 or 5 radicals selected from fluorine, chlorine,            C₁-C₄-alkyl such as methyl, or C₁-C₄-alkoxycarbonyl, or            phenyl, optionally substituted with 1, 2, 3, 4 or 5, in            particular 1, 2 or 3, identical or different substituents            R^(10b), where    -   R^(10b) is as defined above, and in particular selected from the        group consisting of halogen, such as fluorine or chlorine,        C₁-C₄-alkyl, CN, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy.

According to the third group of embodiments C, even more particularpreference is given to compounds of formula (I), wherein R³ and R⁵together form O—C₁-C₃-alkylene, wherein 1, 2, 3 or 4 of the hydrogenatoms in C₁-C₃-alkylene may be replaced by R^(7b), thereby forming,together with the carbon atom they are bound to, an unsubstituted orsubstituted saturated 3-, 4- or 5-membered heterocyclic radical having 1oxygen atom as ring member. According to the third group of embodimentsC, even more particular preference is given to compounds of formula (I),wherein R³ and R⁵ together form O—CH₂ or O—CH₂CH₂, wherein 1, 2, 3 or 4of the hydrogen atoms in CH₂ or CH₂CH₂, may be replaced by R^(7b),thereby forming, together with the carbon atom they are bound to, anunsubstituted or substituted oxiran-2,2-diyl or oxetan-2,2-diyl.

According to a fourth group of embodiments D, compounds of formula (I)are preferred, wherein R³ and R⁵ together form ═S or ═O, in particular═O.

Preferred are compounds of formulae (I) and (Ia), wherein W¹-W²-W³-W⁴represents a carbon chain group connected to N and C═N, which isselected from the group consisting of CR^(w6)═CR^(w5)—CR^(w4)═CR^(w3),CR^(w6)═CR^(w5)—CHR^(w4)—CHR^(w3), CHR^(w6)—CHR^(w5)—CHR^(w4)—CHR^(w3),CHR^(w6)—CHR^(w5)—CR^(w4)═CR^(w3), andCHR^(w6)—CHR^(w5)—CHR^(w4)—CHR^(w3), where in the five aforementionedradicals the carbon atom which carries R^(w6) is bound to the nitrogenatom and where R^(w3), R^(w4), R^(w5) and R^(w6), independently of eachother, have one of the meanings given for R^(w). In this context, R^(w)is preferably selected from the group consisting of hydrogen, halogen,such as fluorine or chlorine, CN, C₁-C₄-alkyl, such as methyl, ethyl,n-propyl and isopropyl, C₁-C₄-haloalkyl, in particular C₁-C₂-haloalkyl,such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy. Preferably, at most one of R^(w3), R^(w4), R^(w5)and R^(w6) is different from hydrogen.

In a particularly preferred group of embodiments R^(w3), R^(w4) andR^(w6) are hydrogen while R^(w5) has one of the meanings given forR^(w), and where R^(w5) is in particular selected from the groupconsisting of hydrogen, halogen, such as fluorine or chlorine, CN,C₁-C₄-alkyl, such as methyl, ethyl, n-propyl and isopropyl,C₁-C₄-haloalkyl, in particular C₁-C₂-haloalkyl, such as fluoromethyl,difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,2,2-difluoroethyl or 2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such asmethoxy, ethoxy, n-propoxy and isopropoxy, and C₁-C₄-haloalkoxy, inparticular C₁-C₂-haloalkoxy, such as fluoromethoxy, difluoromethoxy,trifluoromethoxy, 1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxyor 2,2,2-trifluoroethoxy.

In another particularly preferred group of embodiments R^(w3), R^(w4)and R^(w5) are hydrogen while R^(w6) has one of the meanings given forR^(w), and where R^(w6) is in particular selected from the groupconsisting of hydrogen, halogen, such as fluorine or chlorine, CN,C₁-C₄-alkyl, such as methyl, ethyl, n-propyl and isopropyl,C₁-C₄-haloalkyl, in particular C₁-C₂-haloalkyl, such as fluoromethyl,difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,2,2-difluoroethyl or 2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such asmethoxy, ethoxy, n-propoxy and isopropoxy, and C₁-C₄-haloalkoxy, inparticular C₁-C₂-haloalkoxy, such as fluoromethoxy, difluoromethoxy,trifluoromethoxy, 1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxyor 2,2,2-trifluoroethoxy.

Especially, all of R^(w3), R^(w4), R^(w5) and R^(w6) are hydrogen.

Preferred are compounds of formulae (I) and (Ia), wherein the moiety ofthe formula (A)

represents a radical selected from the group consisting of W.Het-1,W.Het-2, W.Het-3, W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9,W.Het-10, W.Het-11 and W.Het-12, in where the radical of formula (A) isin particular selected from the radicals W.Het-1, W.Het-2, W.Het-5,W.Het-6, W.Het-9 and W.Het-10.

wherein # denotes the bond to the remainder of the molecule and whereR¹, R² and Het are as defined herein and where R¹, R² and Het,individually or in combination have the meanings given as preferredmeanings, and wherein R^(w3), R^(w4), R^(w5) and R^(w6) are as definedabove and in particular selected from the group consisting of hydrogen,halogen, such as fluorine or chlorine, CN, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy.

Particularly preferred are compounds of formulae (I) and (Ia), whereinthe moiety of the formula A is selected from the group consisting ofW.Het-1, W.Het-5 and W.Het-9, wherein R^(w6) is as defined above and inparticular selected from the group consisting of hydrogen, halogen, suchas fluorine or chlorine, CN, C₁-C₄-alkyl, such as methyl, ethyl,n-propyl and isopropyl, C₁-C₄-haloalkyl, in particular C₁-C₂-haloalkyl,such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy and where R^(w6) is especially hydrogen.

Likewise, particularly preferred are compounds of formulae (I) and (Ia),wherein the moiety of the formula A is selected from the groupconsisting of W.Het-2, W.Het-6 and W.Het-10, wherein R^(w5) is asdefined above and in particular selected from the group consisting ofhydrogen, halogen, such as fluorine or chlorine, CN, C₁-C₄-alkyl, suchas methyl, ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy and where R^(w5) is especially hydrogen.

Likewise, particularly preferred are compounds of formulae (I) and (Ia),wherein the moiety of the formula A is selected from the groupconsisting of W.Het-1, W.Het-2, W.Het-3 and W.Het-4, especially from thegroup consisting of W.Het-1 and W.Het-2, wherein R^(w3), R^(w4), R^(w5)and R^(w6), independently of each other, are as defined above and inparticular selected from the group consisting of hydrogen, halogen, suchas fluorine or chlorine, CN, C₁-C₄-alkyl, such as methyl, ethyl,n-propyl and isopropyl, C₁-C₄-haloalkyl, in particular C₁-C₂-haloalkyl,such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy and where at most one of R^(w3), R^(w4), R^(w5)and R^(w6) are especially hydrogen.

In the moieties W.Het-1, W.Het-2, W.Het-3, W.Het-4, W.Het-5, W.Het-6,W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11 and W.Het-12, theheterocycle Het is in particular selected from the group consisting ofthe radicals of formulae Het-1 to Het-24, as defined above, and inparticular selected from the group consisting of the radicals of theformulae Het-1 or Het-1a, Het-11a and Het-24.

In the moieties W.Het-1, W.Het-2, W.Het-3, W.Het-4, W.Het-5, W.Het-6,W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11 and W.Het-12, the radicalsR¹ and R² are, independently from each other, in particular selectedfrom the group consisting of hydrogen, halogen, such as fluorine orchlorine, CN, C₁-C₆-alkyl, in particular C₁-C₄-alkyl, such as methyl,ethyl, n-propyl or isopropyl, C₃-C₆-cycloalkyl, such as cyclopropyl orcyclobutyl, C₁-C₆-haloalkyl, in particular C₁-C₂-haloalkyl, such asfluoromethyl, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl,2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, orC₃-C₆-halocycloalkyl such as 1-fluorocyclopropyl or2,2-difluorocyclopropyl, or R¹ and R² may together be ═CR¹³R¹⁴ or R¹ andR² form, together with the carbon atom, which they attached to, a 3- to5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl orcyclopentyl.

In particular embodiments of moieties W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12, the radicals R¹ and R² are, independently from each other,more particularly selected from the group consisting of hydrogen,halogen, cyano, C₁-C₃-alkyl, such as methyl ethyl or isopropyl, orC₁-C₃-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, where in particular at least one of the radicalsR¹ and R² is hydrogen.

Especially, R¹ and R² in the moieties W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12 are both hydrogen.

A particular group 1 of embodiments relates to compounds of the formulae(I) and (Ia), to their stereoisomers, their tautomers and their salts,wherein the moiety of formula (A) represents a radical selected from thegroup consisting of W.Het-1, wherein Het is selected from the groupconsisting of radicals of formulae Het-1, Het-11a and Het-24.

A further particular group 2 of embodiments relates to compounds of theformulae (I) and (Ia), to their stereoisomers, their tautomers and theirsalts, wherein the moiety of formula (A) represents a radical selectedfrom the group consisting of W.Het-2, wherein Het is selected from thegroup consisting of radicals of formulae Het-1, Het-11a and Het-24.

A further particular group 3 of embodiments relates to compounds of theformulae (I) and (Ia), to their stereoisomers, their tautomers and theirsalts, wherein the moiety of formula (A) represents a radical selectedfrom the group consisting of W.Het-5, wherein Het is selected from thegroup consisting of radicals of formulae Het-1, Het-11a and Het-24.

A further particular group 4 of embodiments relates to compounds of theformulae (I) and (Ia), to their stereoisomers, their tautomers and theirsalts, wherein the moiety of formula (A) represents a radical selectedfrom the group consisting of W.Het-6, wherein Het is selected from thegroup consisting of radicals of formulae Het-1, Het-11a and Het-24.

A further particular group 5 of embodiments relates to compounds of theformulae (I) and (Ia), to their stereoisomers, their tautomers and theirsalts, wherein the moiety of formula (A) represents a radical selectedfrom the group consisting of W.Het-9, wherein Het is selected from thegroup consisting of radicals of formulae Het-1, Het-11a and Het-24.

A further particular group 6 of embodiments relates to compounds of theformulae (I) and (Ia), to their stereoisomers, their tautomers and theirsalts, wherein the moiety of formula (A) represents a radical selectedfrom the group consisting of W.Het-10, wherein Het is selected from thegroup consisting of radicals of formulae Het-1, Het-11a and Het-24.

A special group 1a of embodiments relates to compounds of the formulae(I) and (Ia), to their stereoisomers, their tautomers and their salts,wherein the moiety of formula (A) represents a radical selected from thegroup consisting of W.Het-1, wherein Het is a radicals of formulaeHet-1a.

A further special group 2a of embodiments relates to compounds of theformulae (I) and (Ia), to their stereoisomers, their tautomers and theirsalts, wherein the moiety of formula (A) represents a radical selectedfrom the group consisting of W.Het-2, wherein Het is a radicals offormulae Het-1a.

A further special group 3a of embodiments relates to compounds of theformulae (I) and (Ia), to their stereoisomers, their tautomers and theirsalts, wherein the moiety of formula (A) represents a radical selectedfrom the group consisting of W.Het-5, wherein Het is a radicals offormulae Het-1a.

A further special group 4a of embodiments relates to compounds of theformulae (I) and (Ia), to their stereoisomers, their tautomers and theirsalts, wherein the moiety of formula (A) represents a radical selectedfrom the group consisting of W.Het-6, wherein Het is a radicals offormulae Het-1a.

A further special group 5a of embodiments relates to compounds of theformulae (I) and (Ia), to their stereoisomers, their tautomers and theirsalts, wherein the moiety of formula (A) represents a radical selectedfrom the group consisting of W.Het-9, wherein Het is a radicals offormulae Het-1a.

A further special group 6a of embodiments relates to compounds of theformulae (I) and (Ia), to their stereoisomers, their tautomers and theirsalts, wherein the moiety of formula (A) represents a radical selectedfrom the group consisting of W.Het-10, wherein Het is a radicals offormulae Het-1a.

In embodiments 1, 3, 5, 1a, 3a and 5a the radical R^(w6) is as definedabove and in particular selected from the group consisting of hydrogen,halogen, such as fluorine or chlorine, CN, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy. In embodiments 1, 3, 5, 1a, 3a and 5a the radicalR^(w6) is especially hydrogen.

In embodiments 2, 4, 6, 2a, 4a and 6a the radical R^(w5) is as definedabove and in particular selected from the group consisting of hydrogen,halogen, such as fluorine or chlorine, CN, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy. In embodiments 2, 4, 6, 2a, 4a and 6a the radicalR^(w5) is especially hydrogen.

In embodiments 1, 2, 3, 4, 5, 6, 1a, 2a, 3a, 4a, 5a and 6a the radicalsR¹ and R² are, independently from each other, in particular selectedfrom the group consisting of hydrogen, halogen, such as fluorine orchlorine, CN, C₁-C₆-alkyl, in particular C₁-C₄-alkyl, such as methyl,ethyl, n-propyl or isopropyl, C₃-C₆-cycloalkyl, such as cyclopropyl orcyclobutyl, C₁-C₆-haloalkyl, in particular C₁-C₂-haloalkyl, such asfluoromethyl, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl,2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, orC₃-C₆-halocycloalkyl such as 1-fluorocyclopropyl or2,2-difluorocyclopropyl, or R¹ and R² may together be ═CR¹³R¹⁴ or R¹ andR² form, together with the carbon atom, which they attached to, a 3- to5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl orcyclopentyl.

In embodiments 1, 2, 3, 4, 5, 6, 1a, 2a, 3a, 4a, 5a and 6a the radicalsR¹ and R² are, independently from each other, more particularly selectedfrom the group consisting of hydrogen, halogen, cyano, C₁-C₃-alkyl, suchas methyl ethyl or isopropyl, or C₁-C₃-haloalkyl such as fluoromethyl,difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,2,2-difluoroethyl or 2,2,2-trifluoroethyl, where in particular at leastone of the radicals R¹ and R² is hydrogen and where especially both R¹and R² are hydrogen.

In the compounds of formula (I), where the moiety of formula (A) isselected from the moieties of formulae W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12 and likewise in the embodiments 1, 2, 3, 4, 5, 6, 1a, 2a,3a, 4a, 5a and 6a, the variables m, R¹, R², R³, R^(4a), R^(4b) and R⁵are as defined above and in particular have the preferred meanings.

In the compounds of formula (I), where the moiety of formula (A) isselected from the moieties of formulae W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12 and likewise in the embodiments 1, 2, 3, 4, 5, 6, 1a, 2a,3a, 4a, 5a and 6a, the variables m, R¹, R², R³, R^(4a), R^(4b) and R⁵,independently of each other or in particular in combination, inparticular have the following meanings:

-   -   m is 0 or 1;    -   R¹ and R² are, independently from each other, selected from the        group consisting of hydrogen, halogen, such as fluorine or        chlorine, CN, C₁-C₆-alkyl, in particular C₁-C₄-alkyl, such as        methyl, ethyl, n-propyl or isopropyl, C₃-C₆-cycloalkyl, such as        cyclopropyl or cyclobutyl, C₁-C₆-haloalkyl, in particular        C₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl,        trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,        2,2-difluoroethyl or 2,2,2-trifluoroethyl, or        C₃-C₆-halocycloalkyl such as 1-fluorocyclopropyl or        2,2-difluorocyclopropyl, or R¹ and R² may together be ═CR¹³R¹⁴        or R¹ and R² form, together with the carbon atom, which they        attached to, a 3- to 5 membered saturated carbocyclic ring such        as cyclopropyl, cyclobutyl or cyclopentyl;    -   R³ is selected from the group consisting of hydrogen, halogen,        CN, C₁-C₆-alkyl, in particular C₁-C₄-alkyl, C₁-C₆-haloalkyl, in        particular C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, such as        cyclopropyl or cyclobutyl, C₃-C₆-halocycloalkyl, such as        1-fluorocyclopropyl, 2-fluorocyclopropyl,        2,2-difluorocyclopropyl, 2-chlorocyclopropyl,        2,2-dichlorocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl,        3-fluorocyclobutyl, 2,2-difluorocyclobutyl or        3,3-difluorocyclobutyl, NR^(9a)R^(9b) and NR^(9a)—C(═O)R^(7a),        where R^(7a), R^(9a) and R^(9b) are as defined above and in        particular have the preferred meanings;    -   R⁵ is selected from the group consisting of hydrogen, halogen,        CN, NR^(9a)R^(9b), C₁-C₆-alkyl, in particular C₁-C₄-alkyl,        C₁-C₆-haloalkyl, in particular C₁-C₄-haloalkyl,        C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C(═O)OR⁸,        C(═O)NR^(9a)R^(9b), C(═S)NR^(9a)R^(9b), C(═O)R^(7a),        C(═S)R^(7a), Q-phenyl, where phenyl is unsubstituted or        substituted with 1, 2, 3, 4 or 5 identical or different        substituents R¹⁰, or Q-Het^(#), where Het^(#) is unsubstituted        or substituted with 1, 2, 3, 4 or 5 identical or different        substituents R¹⁰, and where Q, irrespectively of its occurrence,        is a bond, NR^(9a), such as NH or N(CH₃)        -   NR^(9a)—C(═O), such as NH—C(═O)H, NH—C(═O)CH₃,            NH—C(═O)CH₂CH₃ or NH—C(═O)CH(CH₃)₂, OC(═O), NR^(9a)CH₂, such            as NHCH₂ or N(CH₃)CH₂, OC(═O)CH₂, or NR^(9a)C(═O)CH₂ such as            NHC(═O)CH₂,        -   where R^(7a), R^(9a), R^(9b) and R¹⁰ are as defined above            and in particular have the preferred meanings;    -   and if m=1    -   R^(4a) and R^(4b) are selected, independently from one another,        from the group consisting of hydrogen, C₁-C₄-alkyl, in        particular methyl, and halogen, in particular fluorine or        chlorine, or R^(4a) and R^(4b) together are ═O.

In the compounds of formula (I), where the moiety of formula (A) isselected from the moieties of formulae W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12 and likewise in the embodiments 1, 2, 3, 4, 5, 6, 1a, 2a,3a, 4a, 5a and 6a, the variables m, R¹, R², R³, R^(4a), R^(4b) and R⁵,independently of each other or in particular in combination, moreparticularly have the following meanings:

-   -   R¹ and R² are, independently from each other, selected from the        group consisting of hydrogen, halogen, cyano, C₁-C₃-alkyl, such        as methyl ethyl or isopropyl, or C₁-C₃-haloalkyl such as        fluoromethyl, difluoromethyl, trifluoromethyl,        1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or        2,2,2-trifluoroethyl, where in particular at least one of the        radicals R¹ and R² is hydrogen and where especially both R¹ and        R² are hydrogen;    -   R³ is selected from the group consisting of hydrogen, fluorine,        chlorine, C₁-C₄-alkyl, such as methyl, ethyl, n-propyl,        isopropyl or n-butyl, NHC(═O)—C₁-C₄-alkyl, such as NH—C(═O)H,        NH—C(═O)CH₃, NH—C(═O)CH₂CH₃ or NH—C(═O)CH(CH₃)₂, and CN, and in        particular selected from the group of hydrogen and C₁-C₄-alkyl,        such as methyl, ethyl, n-propyl, isopropyl or n-butyl;    -   R⁵ is selected from the group consisting of hydrogen, halogen,        such as fluorine or chlorine, CN, C₁-C₆-alkyl, in particular        C₁-C₄-alkyl, such as methyl, ethyl, n-propyl, isopropyl,        n-butyl, 2-butyl or isobutyl, C₁-C₆-haloalkyl, in particular        C₁-C₄-haloalkyl, such as fluoromethyl, difluoromethyl,        trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,        2,2-difluoroethyl or 2,2,2-trifluoroethyl, C₃-C₆-cycloalkyl,        such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,        C₃-C₆-halocycloalkyl, such as 1-fluorocyclopropyl,        2-fluorocyclopropyl, 2,2-difluorocyclopropyl,        2-chlorocyclopropyl, 2,2-dichlorocyclopropyl,        1-fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl,        2,2-difluorocyclobutyl or 3,3-difluorocyclobutyl, and phenyl,        which is unsubstituted or carries 1, 2, 3, 4 or 5 identical or        different substituents R¹⁰, where R¹⁰ is as defined above and in        particular selected from the group consisting of halogen, such        as chlorine or fluorine, CN, C₁-C₄-alkyl, such as methyl, ethyl,        n-propyl and isopropyl, C₁-C₄-haloalkyl, in particular        C₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl,        trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,        2,2-difluoroethyl or 2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as        methoxy, ethoxy, n-propoxy and isopropoxy, and C₁-C₄-haloalkoxy,        in particular C₁-C₂-haloalkoxy, such as fluoromethoxy,        difluoromethoxy, trifluoromethoxy, 1,1-difluoroethoxy,        2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy;    -   and if m=1    -   R^(4a) and R^(4b) are selected, independently from one another,        from the group consisting of hydrogen and methyl or R^(4a) and        R^(4b) together are ═O.

In the compounds of formula (I), where the moiety of formula (A) isselected from the moieties of formulae W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12 and likewise in the embodiments 1, 2, 3, 4, 5, 6, la, 2a,3a, 4a, 5a and 6a, where m=0, the variables R¹, R², R³, and R⁵,independently of each other or in particular in combination, inparticular may also have the following meanings:

-   R¹ and R² are, independently from each other, selected from the    group consisting of hydrogen, halogen, such as fluorine or chlorine,    CN, C₁-C₆-alkyl, in particular C₁-C₄-alkyl, such as methyl, ethyl,    n-propyl or isopropyl, C₃-C₆-cycloalkyl, such as cyclopropyl or    cyclobutyl, C₁-C₆-haloalkyl, in particular C₁-C₂-haloalkyl, such as    fluoromethyl, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl,    2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or    C₃-C₆-halocycloalkyl such as 1-fluorocyclopropyl or    2,2-difluorocyclopropyl, or R¹ and R² may together be ═CR¹³R¹⁴ or R¹    and R² form, together with the carbon atom, which they attached to,    a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl,    cyclobutyl or cyclopentyl;-   R³ and R⁵ together with the carbon atom, to which they are bound,    form a 3, 4, 5 or 6 membered saturated carbocycle, wherein each of    the carbon atoms of the carbocycle may be unsubstituted or may carry    1, 2, 3, 4, 5 or 6 radicals R^(7b), wherein R^(7b) is as defined    above and wherein    -   R^(7b) is in particular selected from the group consisting of        -   halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, and C₂-C₆-alkynyl, and            wherein the carbon atoms of the aforementioned aliphatic            radicals may optionally be partly or completely halogenated            and/or substituted by a radical selected from C₁-C₄-alkoxy,            C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyloxy,            C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-alkylsulfanyl,            C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, phenoxy, 5- or            6-membered saturated heterocyclyl having 1 heteroatom            selected from O and S, such as tetrahydropyranyl,            tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or            6-membered saturated heterocyclyl may be unsubstituted or            carry 1 or 2 radicals selected from C₁-C₄-alkyl and            C₁-C₄-alkoxy, and wherein one or two radicals R^(7b) may            also be C₃-C₈-cycloalkyl, in particular C₃-C₆-cycloalkyl,            which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals            selected from fluorine, chlorine, C₁-C₄-alkyl such as methyl            and C₁-C₄-alkoxycarbonyl such as methoxycarbonyl,        -   C₃-C₆-cycloalkenyl, which is unsubstituted or carries 1, 2,            3, 4 or 5 radicals selected from fluorine, chlorine or            C₁-C₄-alkyl such as methyl,        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different substituents R^(10b), or        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            such as tetrahydrofuryl, tetrahydropyranyl,            tetrahydrothiopyranyl or thiazolyl, where the heterocyclic            ring is optionally substituted with 1, 2, 3 or 4 identical            or different substituents R^(10b), and wherein the nitrogen            and/or the sulfur atom(s) of the heterocyclic ring may            optionally be oxidized, in particular a 5- or 6-membered            hetaryl having 1 or 2 heteroatoms selected from O, S and N,            where the 5- or 6-membered hetaryl is unsubstituted or            carries 1, 2 or 3 identical or different substituents            R^(10b),        -   or two of R^(7b) present on one ring carbon may together            form ═O or ═S,        -   or two R^(7b) together form a linear C₂-C₇ alkylene chain,            thus forming, together with the carbon atom to which they            are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or            2 CH₂ moieties of the alkylene chain may be replaced by 1 or            2 heteroatom moieties selected from O and S, and where the            alkylene chain is unsubstituted or may be substituted with            1, 2, 3, 4, 5 or 6 radicals selected from the group            consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, where        -   R^(10b) has one of the meanings give for R¹⁰ and where            R^(10b) is in particular selected from the group consisting            of halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy,    -   R^(7b) is more particularly selected from the group consisting        of halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, and C₂-C₆-alkynyl, and        wherein the carbon atoms of the aforementioned aliphatic        radicals may optionally be partly or completely halogenated, and        wherein one or two radicals R^(7b) may also be        -   C₃-C₆-cycloalkyl, which is unsubstituted or carries 1, 2, 3,            4 or 5 radicals selected from fluorine, chlorine or methyl,        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different substituents R^(10b), or a        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is optionally substituted with            1, 2, 3 or 4 identical or different substituents R^(10b),            and wherein the nitrogen and/or the sulfur atom(s) of the            heterocyclic ring may optionally be oxidized, in particular            a 5- or 6-membered hetaryl having 1 or 2 heteroatoms            selected from O, S and N, where the 5- or 6-membered hetaryl            is unsubstituted or carries 1, 2 or 3 identical or different            substituents R^(10a),        -   or two of R^(7b) present on one ring carbon may together            form ═O or ═S,        -   or two R^(7b) together form a linear C₂-C₇ alkylene chain,            thus forming, together with the carbon atom to which they            are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or            2 CH₂ moieties of the alkylene chain may be replaced by 1 or            2 heteroatom moieties selected from O and S, and where the            alkylene chain is unsubstituted or may be substituted with            1, 2, 3, 4, 5 or 6 radicals selected from the group            consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, where    -   R^(10b) has one of the meanings give for R¹⁰ and where R^(10b)        is in particular selected from the group consisting of halogen,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

In the compounds of formula (I), where the moiety of formula (A) isselected from the moieties of formulae W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12 and likewise in the embodiments 1, 2, 3, 4, 5, 6, la, 2a,3a, 4a, 5a and 6a, where m=0, the variables R¹, R², R³, and R⁵,independently of each other or in particular in combination, moreparticular may also have the following meanings:

-   R¹ and R² are, independently from each other, selected from the    group consisting of hydrogen, halogen, cyano, C₁-C₃-alkyl, such as    methyl ethyl or isopropyl, or C₁-C₃-haloalkyl such as fluoromethyl,    difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,    2,2-difluoroethyl or 2,2,2-trifluoroethyl, where in particular at    least one of the radicals R¹ and R² is hydrogen and where especially    both R¹ and R² are hydrogen;-   R³ and R⁵ together with the carbon atom, to which they are bound,    form a 3 or 4 membered saturated carbocycle, i.e. a    1,1-cyclopropylidene or 1,1-cyclobutylidene radical, wherein each of    the carbon atoms of the carbocycle may be unsubstituted or may carry    1, 2, 3, 4, 5 or 6 radicals R^(7b), wherein    -   R^(7b) is as defined above and in particular selected from the        group consisting of        -   halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, and C₂-C₆-alkynyl, and            wherein the carbon atoms of the aforementioned aliphatic            radicals may optionally be partly or completely halogenated            and/or substituted by a radical selected from C₁-C₄-alkoxy,            C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyloxy,            C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-alkylsulfanyl,            C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, phenoxy, 5- or            6-membered saturated heterocyclyl having 1 heteroatom            selected from O and S, such as tetrahydropyranyl,            tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or            6-membered saturated heterocyclyl may be unsubstituted or            carry 1 or 2 radicals selected from C₁-C₄-alkyl and            C₁-C₄-alkoxy, and wherein one or two radicals R^(7b) may            also be C₃-C₈-cycloalkyl, in particular C₃-C₆-cycloalkyl,            which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals            selected from fluorine, chlorine, C₁-C₄-alkyl such as methyl            and C₁-C₄-alkoxycarbonyl such as methoxycarbonyl,        -   C₃-C₆-cycloalkenyl, which is unsubstituted or carries 1, 2,            3, 4 or 5 radicals selected from fluorine, chlorine or            C₁-C₄-alkyl such as methyl,        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different substituents R^(10b), or        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            such as tetrahydrofuryl, tetrahydropyranyl,            tetrahydrothiopyranyl or thiazolyl, where the heterocyclic            ring is optionally substituted with 1, 2, 3 or 4 identical            or different substituents R^(10b), and wherein the nitrogen            and/or the sulfur atom(s) of the heterocyclic ring may            optionally be oxidized, in particular a 5- or 6-membered            hetaryl having 1 or 2 heteroatoms selected from O, S and N,            where the 5- or 6-membered hetaryl is unsubstituted or            carries 1, 2 or 3 identical or different substituents            R^(10b),        -   or two of R^(7b) present on one ring carbon may together            form ═O or ═S,        -   or two R^(7b) together form a linear C₂-C₇ alkylene chain,            thus forming, together with the carbon atom to which they            are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or            2 CH₂ moieties of the alkylene chain may be replaced by 1 or            2 heteroatom moieties selected from O and S, and where the            alkylene chain is unsubstituted or may be substituted with            1, 2, 3, 4, 5 or 6 radicals selected from the group            consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, where        -   R^(10b) has one of the meanings give for R¹⁰ and where            R^(10b) is in particular selected from the group consisting            of halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, or    -   R^(7b) is especially selected from the group consisting of        particular selected from the group consisting of halogen,        C₁-C₄-alkyl, and wherein one radical R^(7b) may also be phenyl,        optionally substituted with 1, 2, 3, 4 or 5, in particular 1, 2        or 3, identical or different substituents R^(10b), where    -   R^(10b) is as defined above, and in particular selected from the        group consisting of halogen, such as fluorine or chlorine,        C₁-C₄-alkyl, CN, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy.

In the compounds of formula (I), where the moiety of formula (A) isselected from the moieties of formulae W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12 and likewise in the embodiments 1, 2, 3, 4, 5, 6, la, 2a,3a, 4a, 5a and 6a, where m=0, the variables R¹, R², R³, and R⁵,independently of each other or in particular in combination, especiallymay also have the following meanings:

-   R¹ and R² are hydrogen or one of R¹ and R² is hydrogen and the other    of R¹ and R² is methyl;-   R³ and R⁵ together form the following moieties:    CH₂—CH₂, CHF—CH₂, CF₂—CH₂, CHF—CHF, CF₂—CHF, CF₂—CF₂, CHCl—CH₂,    CCl₂—CH₂, CHCl—CHCl, CCl₂—CHCl, CCl₂—CCl₂, CH(CH₃)—CH₂, C(CH₃)₂—CH₂,    CH(CH₃)—CH(CH₃), C(CH₃)₂—CH(CH₃), C(CH₃)₂—C(CH₃)₂, CH(OCH₃)—CH₂,    CH(CH₂CH₃)—CH₂, CH(CH₂CH₂CH₃)—CH₂, CH(CH₂CH₂CH₂CH₃)—CH₂,    CH(CH₃)—CH₂—CH₂, CH₂—CH(CH₃)—CH₂, C(CH₃)₂—CH₂—CH₂, CH₂—C(CH₃)₂—CH₂,    CH(CH₃)—CH(CH₃)—CH₂, CH(CH₃)—CH₂—CH(CH₃), CH(CH₃)—CH(CH₃)—CH(CH₃),    C(CH₃)₂—CH(CH₃)—CH₂, CH(CH₃)—C(CH₃)₂—CH₂, C(CH₃)₂—CH₂—C(CH₃)₂,    C(CH₃)₂—C(CH₃)₂—CH₂, C(CH₃)₂—C(CH₃)₂—C(CH₃)₂, CHF—CH₂—CH₂,    CH₂—CHF—CH₂, CF₂—CH₂—CH₂, CH₂—CF₂—CH₂, CHF—CHF—CH₂, CHF—CH₂—CHF,    CHF—CHF—CHF, CF₂—CHF—CH₂, CHF—CF₂—CH₂, CF₂—CH₂—CF₂, CF₂—CF₂—CH₂,    CF₂—CF₂—CF₂, CHCl—CH₂—CH₂, CH₂—CHCl—CH₂, CCl₂—CH₂—CH₂, CH₂—CCl₂—CH₂,    CHCl—CHCl—CH₂, CHCl—CH₂—CHCl, CHCl—CHCl—CHCl, CCl₂—CHCl—CH₂,    CHCl—CCl₂—CH₂, CCl₂—CH₂—CCl₂, CCl₂—CCl₂—CH₂, CCl₂—CCl₂—CCl₂, or a    radical CH(R^(7bb))—CH₂, where R^(7bb) is selected from the group    consisting of    -   C₂-C₁₀-alkyl, such as ethyl, n-propyl, isopropyl, n-butyl,        tert.butyl, 1-methylpropyl, 2-methylpropyl, 1,2-dimethylpropyl,        2,2-dimethylpropyl, 3,3-dimethylpropyl, 1-methylbutyl,        1,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl, 1-ethylpentyl,    -   C₂-C₄-haloalkyl, such as 2,2-difluoroethyl, 1,1-difluoroethyl or        2,2,2-trifluoroethyl,    -   C₁-C₆-alkyl, which is substituted by 1 radical selected from        C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy,        C₁-C₄-alkylsulfanyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy,        phenoxy and 5- or 6-membered saturated heterocyclyl having 1        heteroatom selected from O and S, such as tetrahydropyranyl,        tetrahydrofuranyl, tetrahydrothiopyranyl, where        C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy and 5- or 6-membered        saturated heterocyclyl may be unsubstituted or carry 1 or 2        radicals selected from C₁-C₄-alkyl and C₁-C₄-alkoxy, examples of        substituted C₁-C₆-alkyl including 1-methoxyethyl,        2-methoxyethyl, 1-propoxyethyl, 2-propoxyethyl,        1-isopropoxyethyl, 2-isopropoxyethyl, 1-isobutoxyethyl,        2-isobutoxyethyl, 1-(cyclohexyloxy)ethyl, 2-phenoxyethyl,        (4-isopropylcyclohexyl)methyl, 1-acetoxyethyl, 2-acetoxyethyl,        6-acetoxyhexyl, 2-methylsulfanylpropyl,        1-methyl-2-methylsulfanylethyl, tetrahydropyran-4-ylmethyl,        tetrahydrothiopyran-4-ylmethyl,        -   C₂-C₁₀-alkenyl, such as 3-nonenyl,        -   C₃-C₁₀-cycloalkyl, optionally substituted by 1 or 2            C₁-C₄-alkyl, such as cyclopropyl, cyclobutyl, cyclopentyl,            cyclohexyl, cycloheptyl, cyclooctyl, 4-methylcyclohexyl,            4-isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl,        -   C₅-C₆-cycloalkenyl, optionally substituted by 1 or 2            C₁-C₄-alkyl, such as 2-methylcyclohex-3-en-1-yl,        -   5- or 6-membered saturated heterocyclyl having 1 heteroatom            selected from O and S, such as tetrahydropyranyl,            tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or            6-membered saturated heterocyclyl may be unsubstituted or            carry 1 or 2 radicals selected from C₁-C₄-alkyl and            C₁-C₄-alkoxy, examples including tetrahydrofuran-2-yl,            tetrahydrofuran-3-yl, tetrahydropyran-3-yl,            tetrahydropyran-4-yl, tehtrahydrothiopyran-3-yl,            tetrahydrothiopyran-4-yl,            6-methoxy-3-methyltetrahydropyran-2-yl, and            5,5-dimethyltetrahydrofuran-2-yl,        -   optionally substituted phenyl such as phenyl,            2-chlorophenyl, 2-fluorophenyl, 2-methylphenyl,            2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl,            3-fluorophenyl, 3-methylphenyl, 3-methoxyphenyl,            3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl,            4-methylphenyl, 4-methoxyphenyl, 3-nitrophenyl,            4-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl and            4-cyanophenyl,        -   5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring            members, selected from O, S and N and where the hetaryl is            unsubstituted or substituted by 1 or 2 radicals selected            from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and            C₁-C₄-haloalkoxy examples of hetaryl including            4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl,        -   phenyl-C₁-C₄-alkyl, such as benzyl or phenethyl, and        -   hetaryl-C₁-C₄-alkyl, where the hetaryl is 5- or 6-membered            and has 1 or 2 heteroatoms as ring members, selected from O,            S and N and where the hetaryl is unsubstituted or            substituted by 1 or 2 radicals selected from halogen,            C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and            C₁-C₄-haloalkoxy examples of hetaryl-C₁-C₄-alkyl including            1,1-dimethyl-2-(3-pyridyl)ethyl,            thereby forming, together with the carbon atom they are            bound to, an unsubstituted or substituted            1,1-cyclopropylidene or 1,1-cyclobutylidene radical.

In the compounds of formula (I), where the moiety of formula (A) isselected from the moieties of formulae W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12 and likewise in the embodiments 1, 2, 3, 4, 5, 6, 1a, 2a,3a, 4a, 5a and 6a, where m=0, the variables R¹, R², R³, and R⁵,independently of each other or in particular in combination, especiallymay also have the following meanings:

-   R¹ and R² are hydrogen or one of R¹ and R² is hydrogen and the other    of R¹ and R² is methyl;-   R³ and R⁵ together form a moiety selected from the group consisting    of:    -   CH₂—CH₂, CHF—CH₂, CF₂—CH₂, CHF—CHF, CF₂—CHF, CF₂—CF₂, CHCl—CH₂,        CCl₂—CH₂, CHCl—CHCl, CCl₂—CHCl, CCl₂—CCl₂, CH(CH₃)—CH₂,        C(CH₃)₂—CH₂, CH(CH₃)—CH(CH₃), C(CH₃)₂—CH(CH₃), C(CH₃)₂—C(CH₃)₂,        CH(OCH₃)—CH₂, CH(CH₂CH₃)—CH₂, CH(CH₂CH₂CH₃)—CH₂,        CH(CH₂CH₂CH₂CH₃)—CH₂, CH(CH₃)—CH₂—CH₂, CH₂—CH(CH₃)—CH₂,        C(CH₃)₂—CH₂—CH₂, CH₂—C(CH₃)₂—CH₂, CH(CH₃)—CH(CH₃)—CH₂,        CH(CH₃)—CH₂—CH(CH₃), CH(CH₃)—CH(CH₃)—CH(CH₃),        C(CH₃)₂—CH(CH₃)—CH₂, CH(CH₃)—C(CH₃)₂—CH₂, C(CH₃)₂—CH₂—C(CH₃)₂,        C(CH₃)₂—C(CH₃)₂—CH₂, C(CH₃)₂—C(CH₃)₂—C(CH₃)₂, CHF—CH₂—CH₂,        CH₂—CHF—CH₂, CF₂—CH₂—CH₂, CH₂—CF₂—CH₂, CHF—CHF—CH₂, CHF—CH₂—CHF,        CHF—CHF—CHF, CF₂—CHF—CH₂, CHF—CF₂—CH₂, CF₂—CH₂—CF₂, CF₂—CF₂—CH₂,        CF₂—CF₂—CF₂, CHCl—CH₂—CH₂, CH₂—CHCl—CH₂, CCl₂—CH₂—CH₂,        CH₂—CCl₂—CH₂, CHCl—CHCl—CH₂, CHCl—CH₂—CHCl, CHCl—CHCl—CHCl,        CCl₂—CHCl—CH₂, CHCl—CCl₂—CH₂, CCl₂—CH₂—CCl₂, CCl₂—CCl₂—CH₂,        CCl₂—CCl₂—CCl₂ or a radical CH(Ar)—CH₂, where Ar is selected        from phenyl, 2-chlorophenyl, 2-fluorophenyl, 2-methylphenyl,        2-methoxyphenyl, 2-cyanophenyl, 3-chlorophenyl, 3-fluorophenyl,        3-methylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 4-chlorophenyl,        4-fluorophenyl, 4-methylphenyl, 4-methoxyphenyl and        4-cyanophenyl, thereby forming, together with the carbon atom        they are bound to, an unsubstituted or substituted        1,1-cyclopropylidene or 1,1-cyclobutylidene radical.

Special preference is given to compounds of formula (Ia) and (Ib),

where Het, W¹, W², W³, W⁴ and X, are as defined above and in particularhave the preferred meanings or the particularly preferred meanings;

-   R¹ and R² are, independently from each other, selected from the    group consisting of hydrogen, halogen, cyano, C₁-C₃-alkyl, such as    methyl ethyl or isopropyl, or C₁-C₃-haloalkyl such as fluoromethyl,    difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,    2,2-difluoroethyl or 2,2,2-trifluoroethyl, where in particular at    least one of the radicals R¹ and R² is hydrogen and where especially    both R¹ and R² are hydrogen;-   R^(7b1) is hydrogen or has one of the meanings given for R^(7b);-   R^(7b2), R^(7b3) and R^(7b4) are hydrogen, methyl or halogen, in    particular hydrogen and where-   R^(7b1) is in particular hydrogen or a radical selected from the    group consisting of    -   C₁-C₁₀-alkyl, such as methyl, ethyl, n-propyl, isopropyl,        n-butyl, tert.butyl, 1-methylpropyl, 2-methylpropyl,        1,2-dimethylpropyl, 2,2-dimethylpropyl, 3,3-dimethylpropyl,        1-methylbutyl, 1,2-dimethylbutyl, 3,3-dimethylbutyl, n-pentyl,        1-ethylpentyl,    -   C₁-C₄-haloalkyl, such as difluoromethyl, trifluoromethyl,        2,2-difluoroethyl, 1,1-difluoroethyl or 2,2,2-trifluoroethyl,    -   C₁-C₆-alkyl, which is substituted by 1 radical selected from        C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy,        C₁-C₄-alkylsulfanyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy,        phenoxy and 5- or 6-membered saturated heterocyclyl having 1        heteroatom selected from O and S, such as tetrahydropyranyl,        tetrahydrofuranyl, tetrahydrothiopyranyl, where        C₃-C₈-cycloalkyl, C₃-C₈-cycloalkoxy and 5- or 6-membered        saturated heterocyclyl may be unsubstituted or carry 1 or 2        radicals selected from C₁-C₄-alkyl and C₁-C₄-alkoxy, examples of        substituted C₁-C₆-alkyl including 1-methoxyethyl,        2-methoxyethyl, 1-propoxyethyl, 2-propoxyethyl,        1-isopropoxyethyl, 2-isopropoxyethyl, 1-isobutoxyethyl,        2-isobutoxyethyl, 1-(cyclohexyloxy)ethyl, 2-phenoxyethyl,        (4-isopropylcyclohexyl)methyl, 1-acetoxyethyl, 2-acetoxyethyl,        6-acetoxyhexyl, 2-methylsulfanylpropyl,        1-methyl-2-methylsulfanylethyl, tetrahydropyran-4-ylmethyl,        tetrahydrothiopyran-4-ylmethyl,    -   C₂-C₁₀-alkenyl, such as 3-nonenyl,    -   C₃-C₁₀-cycloalkyl, optionally substituted by 1 or 2 C₁-C₄-alkyl,        such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,        cycloheptyl, cyclooctyl, 4-methylcyclohexyl,        4-isopropylcyclohexyl, and 6,6-dimethylnorpinan-2-yl,    -   C₅-C₆-cycloalkenyl, optionally substituted by 1 or 2        C₁-C₄-alkyl, such as 2-methylcyclohex-3-en-1-yl, 5- or        6-membered saturated heterocyclyl having 1 heteroatom selected        from O and S, such as tetrahydropyranyl, tetrahydrofuranyl and        tetrahydrothiopyranyl, where the 5- or 6-membered saturated        heterocyclyl may be unsubstituted or carry 1 or 2 radicals        selected from C₁-C₄-alkyl and C₁-C₄-alkoxy, examples including        tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,        tetrahydropyran-3-yl, tetrahydropyran-4-yl,        tehtrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl,        6-methoxy-3-methyltetrahydropyran-2-yl, and        5,5-dimethyltetrahydrofuran-2-yl,    -   optionally substituted phenyl such as phenyl, 2-chlorophenyl,        2-fluorophenyl, 2-methylphenyl, 2-methoxyphenyl, 2-cyanophenyl,        3-chlorophenyl, 3-fluorophenyl, 3-methylphenyl, 3-methoxyphenyl,        3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 4-methylphenyl,        4-methoxyphenyl, 3-nitrophenyl, 4-(trifluoromethyl)phenyl,        3-(trifluoromethyl)phenyl and 4-cyanophenyl,    -   5- or 6-membered hetaryl having 1 or 2 heteroatoms as ring        members, selected from O, S and N and where the hetaryl is        unsubstituted or substituted by 1 or 2 radicals selected from        halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy examples of hetaryl including        4-methylthiazol-5-yl, 2-pyridyl and 3-pyridyl,    -   phenyl-C₁-C₄-alkyl, such as benzyl or phenethyl, and    -   hetaryl-C₁-C₄-alkyl, where the hetaryl is 5- or 6-membered and        has 1 or 2 heteroatoms as ring members, selected from O, S and N        and where the hetaryl is unsubstituted or substituted by 1 or 2        radicals selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy and C₁-C₄-haloalkoxy examples of        hetaryl-C₁-C₄-alkyl including 1,1-dimethyl-2-(3-pyridyl)ethyl.

In the compounds of formula (I), where the moiety of formula (A) isselected from the moieties of formulae W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12 and likewise in the embodiments 1, 2, 3, 4, 5, 6, la, 2a,3a, 4a, 5a and 6a, where m=0, the variables R¹, R², R³, and R⁵,independently of each other or in particular in combination, inparticular may also have the following meanings:

-   R¹ and R² are, independently from each other, selected from the    group consisting of hydrogen, halogen, such as fluorine or chlorine,    CN, C₁-C₆-alkyl, in particular C₁-C₄-alkyl, such as methyl, ethyl,    n-propyl or isopropyl, C₃-C₆-cycloalkyl, such as cyclopropyl or    cyclobutyl, C₁-C₆-haloalkyl, in particular C₁-C₂-haloalkyl, such as    fluoromethyl, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl,    2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or    C₃-C₆-halocycloalkyl such as 1-fluorocyclopropyl or    2,2-difluorocyclopropyl, or R¹ and R² may together be ═CR¹³R¹⁴ or R¹    and R² form, together with the carbon atom, which they attached to,    a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl,    cyclobutyl or cyclopentyl;-   R³ and R⁵ together with the carbon atom, to which they are bound,    form a 3, 4, 5 or 6 membered saturated heterocycle having 1 or 2 non    adjacent heteroatoms as ring members which are selected from O and    S, in particular a 3 or 4 membered saturated heterocycle having 1    oxygen atom as ring member wherein the heterocycle may be    unsubstituted or may carry 1, 2, 3, 4, 5 or 6 radicals R^(7b),    wherein R^(7b), if present, is as defined above and wherein    -   R^(7b) if present, is in particular selected from the group        consisting of        -   halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, and C₂-C₆-alkynyl, and            wherein the carbon atoms of the aforementioned aliphatic            radicals may optionally be partly or completely halogenated            and/or substituted by a radical selected from C₁-C₄-alkoxy,            C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyloxy,            C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-alkylsulfanyl,            C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, phenoxy, 5- or            6-membered saturated heterocyclyl having 1 heteroatom            selected from O and S, such as tetrahydropyranyl,            tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or            6-membered saturated heterocyclyl may be unsubstituted or            carry 1 or 2 radicals selected from C₁-C₄-alkyl and            C₁-C₄-alkoxy, and wherein one or two radicals R^(7b) may            also be C₃-C₈-cycloalkyl, in particular C₃-C₆-cycloalkyl,            which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals            selected from fluorine, chlorine, C₁-C₄-alkyl such as methyl            and C₁-C₄-alkoxycarbonyl such as methoxycarbonyl,        -   C₃-C₆-cycloalkenyl, which is unsubstituted or carries 1, 2,            3, 4 or 5 radicals selected from fluorine, chlorine or            C₁-C₄-alkyl such as methyl,        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different substituents R^(10b), or        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            such as tetrahydrofuryl, tetrahydropyranyl,            tetrahydrothiopyranyl or thiazolyl, where the heterocyclic            ring is optionally substituted with 1, 2, 3 or 4 identical            or different substituents R^(10b), and wherein the nitrogen            and/or the sulfur atom(s) of the heterocyclic ring may            optionally be oxidized, in particular a 5- or 6-membered            hetaryl having 1 or 2 heteroatoms selected from O, S and N,            where the 5- or 6-membered hetaryl is unsubstituted or            carries 1, 2 or 3 identical or different substituents            R^(10b),        -   or two of R^(7b) present on one ring carbon may together            form ═O or ═S,        -   or two R^(7b) together form a linear C₂-C₇ alkylene chain,            thus forming, together with the carbon atom to which they            are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or            2 CH₂ moieties of the alkylene chain may be replaced by 1 or            2 heteroatom moieties selected from O and S, and where the            alkylene chain is unsubstituted or may be substituted with            1, 2, 3, 4, 5 or 6 radicals selected from the group            consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, where        -   R^(10b) has one of the meanings give for R¹⁰ and where            R^(10b) is in particular selected from the group consisting            of halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy,    -   R^(7b) is more particularly selected from the group consisting        of halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, and C₂-C₆-alkynyl, and        wherein the carbon atoms of the aforementioned aliphatic        radicals may optionally be partly or completely halogenated, and        wherein one or two radicals R^(7b) may also be        -   C₃-C₆-cycloalkyl, which is unsubstituted or carries 1, 2, 3,            4 or 5 radicals selected from fluorine, chlorine or methyl,        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different substituents R^(10b), or a        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            where the heterocyclic ring is optionally substituted with            1, 2, 3 or 4 identical or different substituents R^(10b),            and wherein the nitrogen and/or the sulfur atom(s) of the            heterocyclic ring may optionally be oxidized, in particular            a 5- or 6-membered hetaryl having 1 or 2 heteroatoms            selected from O, S and N, where the 5- or 6-membered hetaryl            is unsubstituted or carries 1, 2 or 3 identical or different            substituents R^(10a),        -   or two of R^(7b) present on one ring carbon may together            form ═O or ═S,        -   or two R^(7b) together form a linear C₂-C₇ alkylene chain,            thus forming, together with the carbon atom to which they            are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or            2 CH₂ moieties of the alkylene chain may be replaced by 1 or            2 heteroatom moieties selected from O and S, and where the            alkylene chain is unsubstituted or may be substituted with            1, 2, 3, 4, 5 or 6 radicals selected from the group            consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, where    -   R^(10b) has one of the meanings give for R¹⁰ and where R^(10b)        is in particular selected from the group consisting of halogen,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

In the compounds of formula (I), where the moiety of formula (A) isselected from the moieties of formulae W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12 and likewise in the embodiments 1, 2, 3, 4, 5, 6, 1a, 2a,3a, 4a, 5a and 6a, where m=0, the variables R¹, R², R³, and R⁵,independently of each other or in particular in combination, moreparticular may also have the following meanings:

-   R¹ and R² are, independently from each other, selected from the    group consisting of hydrogen, halogen, cyano, C₁-C₃-alkyl, such as    methyl ethyl or isopropyl, or C₁-C₃-haloalkyl such as fluoromethyl,    difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,    2,2-difluoroethyl or 2,2,2-trifluoroethyl, where in particular at    least one of the radicals R¹ and R² is hydrogen and where especially    both R¹ and R² are hydrogen;-   R³ and R⁵ together with the carbon atom, to which they are bound,    form a 3, 4, 5 or 6 membered saturated heterocycle having 1 or 2 non    adjacent heteroatoms as ring members which are selected from O and    S, in particular a 3 or 4 membered saturated heterocycle having 1    oxygen atom as ring member wherein the heterocycle may be    unsubstituted or may carry 1, 2, 3, 4, 5 or 6 radicals R^(7b),    wherein R^(7b), if present, is as defined above and wherein    -   R^(7b) is as defined above and in particular selected from the        group consisting of        -   halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, and C₂-C₆-alkynyl, and            wherein the carbon atoms of the aforementioned aliphatic            radicals may optionally be partly or completely halogenated            and/or substituted by a radical selected from C₁-C₄-alkoxy,            C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyloxy,            C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-alkylsulfanyl,            C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, phenoxy, 5- or            6-membered saturated heterocyclyl having 1 heteroatom            selected from O and S, such as tetrahydropyranyl,            tetrahydrofuranyl and tetrahydrothiopyranyl, where the 5- or            6-membered saturated heterocyclyl may be unsubstituted or            carry 1 or 2 radicals selected from C₁-C₄-alkyl and            C₁-C₄-alkoxy, and wherein one or two radicals R^(7b) may            also be C₃-C₈-cycloalkyl, in particular C₃-C₆-cycloalkyl,            which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals            selected from fluorine, chlorine, C₁-C₄-alkyl such as methyl            and C₁-C₄-alkoxycarbonyl such as methoxycarbonyl,        -   C₃-C₆-cycloalkenyl, which is unsubstituted or carries 1, 2,            3, 4 or 5 radicals selected from fluorine, chlorine or            C₁-C₄-alkyl such as methyl,        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5            identical or different substituents R^(10b), or        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated            or unsaturated aromatic heterocyclic ring comprising 1, 2 or            3 heteroatoms as ring members, which are identical or            different and selected from oxygen, nitrogen and sulfur,            such as tetrahydrofuryl, tetrahydropyranyl,            tetrahydrothiopyranyl or thiazolyl, where the heterocyclic            ring is optionally substituted with 1, 2, 3 or 4 identical            or different substituents R^(10b), and wherein the nitrogen            and/or the sulfur atom(s) of the heterocyclic ring may            optionally be oxidized, in particular a 5- or 6-membered            hetaryl having 1 or 2 heteroatoms selected from O, S and N,            where the 5- or 6-membered hetaryl is unsubstituted or            carries 1, 2 or 3 identical or different substituents            R^(10b),        -   or two of R^(7b) present on one ring carbon may together            form ═O or ═S,        -   or two R^(7b) together form a linear C₂-C₇ alkylene chain,            thus forming, together with the carbon atom to which they            are bound, a 3-, 4-, 5- or 6-membered spiro ring, where 1 or            2 CH₂ moieties of the alkylene chain may be replaced by 1 or            2 heteroatom moieties selected from O and S, and where the            alkylene chain is unsubstituted or may be substituted with            1, 2, 3, 4, 5 or 6 radicals selected from the group            consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, where        -   R^(10b) has one of the meanings give for R¹⁰ and where            R^(10b) is in particular selected from the group consisting            of halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, or    -   R^(7b) is especially selected from the group consisting of        particular selected from the group consisting of halogen,        C₁-C₄-alkyl, and wherein one radical R^(7b) may also be phenyl,        optionally substituted with 1, 2, 3, 4 or 5, in particular 1, 2        or 3, identical or different substituents R^(10b), where    -   R^(10b) is as defined above, and in particular selected from the        group consisting of halogen, such as fluorine or chlorine,        C₁-C₄-alkyl, CN, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy.

In the compounds of formula (I), where the moiety of formula (A) isselected from the moieties of formulae W.Het-1, W.Het-2, W.Het-3,W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11and W.Het-12 and likewise in the embodiments 1, 2, 3, 4, 5, 6, 1a, 2a,3a, 4a, 5a and 6a, where m=0, the variables R¹, R², R³, and R⁵,independently of each other or in particular in combination, especiallymay also have the following meanings:

-   R¹ and R² are hydrogen or one of R¹ and R² is hydrogen and the other    of R¹ and R² is methyl;-   R³ and R⁵ together form O—CH₂ or O—CH₂—CH₂, where 1, 2, 3 or 4 of    the hydrogen atoms of CH₂ and CH₂—CH₂, respectively, may be replaced    by a radical R^(7b), thereby forming, together with the carbon atom    they are bound to, an unsubstituted or substituted    1,1-cyclopropylidene or 1,1-cyclobutylidene radical.

In the compounds of formulae (I) and (Ia), in particular in thosecompounds of formula (I) where the moiety of formula (A) is selectedfrom the moieties of formulae W.Het-1, W.Het-2, W.Het-3, W.Het-4,W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11 andW.Het-12 and likewise in the embodiments 1, 2, 3, 4, 5, 6, 1a, 2a, 3a,4a, 5a and 6a, the variable X is in particular O.

Apart from that, the variables Het^(#), Q, R^(v), R^(w), R⁶, R⁷, R^(7a),R⁸, R^(8a), R⁹, R^(9a), R^(9b), R^(9c), R^(9d), R¹⁰, R^(10a), R¹¹, R¹²,R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R^(17a), R^(17b) and R^(17c), irrespectively oftheir occurrence, in particular have the following meanings, if notstated otherwise:

Het^(#) irrespectively of its occurrence, is 5- or 6-membered hetarylsuch as pyridyl, thienyl, furyl, pyrrolyl, thiazolyl, isothiazolyl,pyrazolyl, imidazolyl, oxazolyl or isoxazolyl, which is unsubstituted orsubstituted by 1, 2 or 3 radicals R¹⁰.

Q is, irrespectively of its occurrence, selected from a single bond,NR^(9a), CH₂, and NR^(9a)CH₂, and it is in particular a single bond, NH,N(C₁-C₄-alkyl, CH₂, NHCH₂ or N(C₁-C₄-alkyl)CH₂.

R^(v) is hydrogen or together with an R^(v), which is bound to anadjacent carbon atom, forms together with the existing bound aC═C-double bond.

R^(w) irrespectively of its occurrence, is selected from the groupconsisting of hydrogen, halogen, such as fluorine or chlorine, CN,C₁-C₄-alkyl, such as methyl, ethyl, n-propyl and isopropyl,C₁-C₄-haloalkyl, in particular C₁-C₂-haloalkyl, such as fluoromethyl,difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl,2,2-difluoroethyl or 2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such asmethoxy, ethoxy, n-propoxy and isopropoxy, and C₁-C₄-haloalkoxy, inparticular C₁-C₂-haloalkoxy, such as fluoromethoxy, difluoromethoxy,trifluoromethoxy, 1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxyor 2,2,2-trifluoroethoxy. R^(w) is more particularly hydrogen, chlorine,fluorine or methyl and especially hydrogen.

R⁶ irrespectively of its occurrence, is selected from the groupconsisting of halogen, such as chlorine or fluorine, C₁-C₄-alkyl, suchas methyl or ethyl, C₁-C₄-alkoxy, such as methoxy or ethoxy,C₁-C₄-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, andC₁-C₄-haloalkyl, such as difluoromethyl, trifluoromethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, morepreferably from halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl, even morepreferably from fluorine, chlorine, C₁-C₂-alkyl, such as methyl or ethyland C₁-C₂-haloalkyl such as difluoromethyl, trifluoromethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.

R⁷ irrespectively of its occurrence, is selected from the groupconsisting of CN, C₁-C₄-alkoxy, such as methoxy or ethoxy,C₁-C₄-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, such asdifluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethylor pentafluoroethyl, more preferably from halogen, C₁-C₄-alkyl andC₁-C₄-haloalkyl, even more preferably from fluorine, chlorine,C₁-C₂-alkyl, such as methyl or ethyl and C₁-C₂-haloalkyl such asdifluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethylor pentafluoroethyl, C₃-C₆-cycloalkyl such as cyclopropyl, cyclobutyl orcyclopropyl, and C₃-C₆-halocycloalkyl.

R^(7a) irrespectively of its occurrence, is selected from the groupconsisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ringin the last two radicals is unsubstituted or substituted by 1, 2 or 3identical or different radicals selected from the group consisting ofhalogen, such as chlorine or fluorine, CN, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy.

R⁸ irrespectively of its occurrence, is selected from the groupconsisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ringin the last two radicals is unsubstituted or substituted by 1, 2 or 3identical or different radicals selected from the group consisting ofhalogen, such as chlorine or fluorine, CN, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy.

R^(8a) irrespectively of its occurrence, is selected from the groupconsisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ringin the last two radicals is unsubstituted or substituted by 1, 2 or 3identical or different radicals selected from the group consisting ofhalogen, such as chlorine or fluorine, CN, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy.

R⁹ irrespectively of its occurrence, is selected from the groupconsisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ringin the last two radicals is unsubstituted or substituted by 1, 2 or 3identical or different radicals selected from the group consisting ofhalogen, such as chlorine or fluorine, CN, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy.

R^(9a) and R^(9b) irrespectively of their occurrence, are preferablyselected from the group consisting of hydrogen, C₁-C₄-alkyl, such asmethyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, andC₁-C₄-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, or NR^(9a)R^(9b) may also be a saturated N-bound3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogenatom may have 1 further heteroatom as ring members, which is selectedfrom O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocyclemay be unsubstituted or carry 1, 2, 3 or 4 radicals selected fromC₁-C₄-alkyl and C₁-C₄-haloalkyl. Examples of such radicals NR^(9a)R^(9b)include, but are not limited to methylamino, ethylamino, n-propylamino,isopropylamino, n-butylamino, 2-butylamino, isobutylamino,dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino,N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino,N-methyl-N-isopropylamino, N-methyl-N-n-butylamino,N-methyl-N-2-butylamino, N-methyl-N-isobutylamino, 1-pyrrolidinyl,1-piperidinyl, 1-piperazinyl, 4-methyl-1-piperazinyl and 4-morpholinyl.

R^(9c) and R^(9d) irrespectively of their occurrence, are preferablyselected from the group consisting of hydrogen, C₁-C₄-alkyl, such asmethyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, andC₁-C₄-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl. Examples of such radicals NR^(9c)R^(9d) include,but are not limited to methylamino, ethylamino, n-propylamino,isopropylamino, n-butylamino, 2-butylamino, isobutylamino,dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino,N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino,N-methyl-N-isopropylamino, N-methyl-N-n-butylamino,N-methyl-N-2-butylamino and N-methyl-N-isobutylamino.

R¹⁰ irrespectively of its occurrence, is selected from the groupconsisting of halogen, such as chlorine or fluorine, CN, C₁-C₄-alkyl,such as methyl, ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, inparticular C₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl,trifluoromethyl, 1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy. R^(10a) irrespectively of its occurrence, isselected from the group consisting of halogen, cyano, NO₂, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, phenyl,optionally substituted with 1, 2, 3, 4 or 5 identical or differentradicals selected from OH, halogen, cyano, nitro, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.

R¹¹, R¹² independently of their occurrence, are selected from the groupconsisting of C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ringin last two radicals are unsubstituted or substituted with 1, 2, or 3identical or different radicals selected from fluorine, chlorine,C₁-C₃-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy and C₁-C₂-haloalkoxy.

R¹³, R¹⁴ independently of their occurrence, are selected from the groupconsisting of hydrogen, fluorine, chlorine, CN, C₁-C₄-alkyl, such asmethyl, ethyl, n-propyl or n-butyl, C₃-C₆-cycloalkyl, such ascyclopropyl, cyclobutyl or cyclopentyl, and phenyl.

R¹⁵ irrespectively of its occurrence, is selected from the groupconsisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ringin the last two radicals is unsubstituted or substituted by 1, 2 or 3identical or different radicals selected from the group consisting ofhalogen, such as chlorine or fluorine, CN, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy.

R¹⁶ irrespectively of its occurrence, is selected from the groupconsisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ringin the last two radicals is unsubstituted or substituted by 1, 2 or 3identical or different radicals selected from the group consisting ofhalogen, such as chlorine or fluorine, CN, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy.

R¹⁷ irrespectively of its occurrence, is selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₁-C₆-alkoxy,C₁-C₄-haloalkoxy, C₃-C₆-alkenyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyland benzyl, where the phenyl ring in the last two radicals isunsubstituted or substituted by 1, 2 or 3 identical or differentradicals selected from the group consisting of halogen, such as chlorineor fluorine, CN, C₁-C₄-alkyl, such as methyl, ethyl, n-propyl andisopropyl, C₁-C₄-haloalkyl, in particular C₁-C₂-haloalkyl, such asfluoromethyl, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl,2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C₁-C₄-alkoxy,such as methoxy, ethoxy, n-propoxy and isopropoxy, and C₁-C₄-haloalkoxy,in particular C₁-C₂-haloalkoxy, such as fluoromethoxy, difluoromethoxy,trifluoromethoxy, 1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxyor 2,2,2-trifluoroethoxy.

R^(17a) and R^(17b) irrespectively of their occurrence, are preferablyselected from the group consisting of hydrogen, C₁-C₄-alkyl, such asmethyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, andC₁-C₄-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, or NR^(9a)R^(9b) may also be a saturated N-bound3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogenatom may have 1 further heteroatom as ring members, which is selectedfrom O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocyclemay be unsubstituted or carry 1, 2, 3 or 4 radicals selected fromC₁-C₄-alkyl and C₁-C₄-haloalkyl. Examples of such radicals NR^(9a)R^(9b)include, but are not limited to methylamino, ethylamino, n-propylamino,isopropylamino, n-butylamino, 2-butylamino, isobutylamino,dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino,N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino,N-methyl-N-isopropylamino, N-methyl-N-n-butylamino,N-methyl-N-2-butylamino, N-methyl-N-isobutylamino, 1-pyrrolidinyl,1-piperidinyl, 1-piperazinyl, 4-methyl-1-piperazinyl and 4-morpholinyl.

R^(17c) irrespectively of its occurrence, is selected from the groupconsisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ringin the last two radicals is unsubstituted or substituted by 1, 2 or 3identical or different radicals selected from the group consisting ofhalogen, such as chlorine or fluorine, CN, C₁-C₄-alkyl, such as methyl,ethyl, n-propyl and isopropyl, C₁-C₄-haloalkyl, in particularC₁-C₂-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl,1,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or2,2,2-trifluoroethyl, C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxyand isopropoxy, and C₁-C₄-haloalkoxy, in particular C₁-C₂-haloalkoxy,such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,1,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or2,2,2-trifluoroethoxy.

A special group of embodiments relates to the compounds of formula(I)-A.1a, to their tautomers, to their stereoisomers and to their salts,where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined above and whereR¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one of themeanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.2a, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.1 b, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.2b, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.1c, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.2c, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.1d, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.2d, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.3a, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.4a, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.3b, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, R[CR^(4a)R^(4b)]_(m) ⁴ and R⁵ have in particular oneof the meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.4b, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.3c, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.4c, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.3d, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.4d, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.5a, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.5b, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.5c, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A further special group of embodiments relates to the compounds offormula (I)-A.5d, to their tautomers, to their stereoisomers and totheir salts, where m, R¹, R³, R^(4a), R^(4b) and R⁵ are as defined aboveand where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have in particular one ofthe meanings given in any of lines 1 to 872 of the following table A.

A skilled person will readily appreciate that the compounds of formulae(I)-A.1a, (I)-A.2a, (I)-A.3a, (I)-A.4a, (I)-A.1b, (I)-A.2b, (I)-A.3b,(I)-A.4b, (I)-A.1c, (I)-A.2c, (I)-A.3c, (I)-A.4c, (I)-A.1d, (I)-A.2d,(I)-A.3d, (I)-A.4d, (I)-A.5a, (I)-A.5b, (I)-A.5c and (I)-A.5d, where R¹,R³, [CR^(4a)R^(4b)]_(m) and R⁵ have the meanings given in one of lines 6to 164, 168 to 308, 333 to 436, 442 to 744 or 769 to 872 of thefollowing table A may have S- or R-configuration with regard to thecarbon atom carrying the radical R³. A skilled person will also readilyappreciate that the compounds of formulae (I)-A.1a, (I)-A.2a, (I)-A.3a,(I)-A.4a, (I)-A.1b, (I)-A.2b, (I)-A.3b, (I)-A.4b, (I)-A.1c, (I)-A.2c,(I)-A.3c, (I)-A.4c, (I)-A.1d, (I)-A.2d, (I)-A.3d, (I)-A.4d, (I)-A.5a,(I)-A.5b, (I)-A.5c and (I)-A.5d, where R¹, R³, [CR^(4a)R^(4b)]_(m) andR⁵ have the meanings given in one of lines 437 to 872 of the followingtable A may have S- or R-configuration with regard to the carbon atomcarrying the radical R¹. A skilled person will also readily appreciatethat the compounds of formulae (I)-A.1a, (I)-A.2a, (I)-A.3a, (I)-A.4a,(I)-A.1b, (I)-A.2b, (I)-A.3b, (I)-A.4b, (I)-A.1c, (I)-A.2c, (I)-A.3c,(I)-A.4c, (I)-A.1d, (I)-A.2d, (I)-A.3d, (I)-A.4d, (I)-A.5a, (I)-A.5b,(I)-A.5c and (I)-A.5d, where R¹, R³, [CR^(4a)R^(4b)]_(m) and R⁵ have themeanings given in one of lines 442 to 744 or 769 to 872 of the followingtable A will form diastereomeric mixtures. The aforementionedembodiments include both the S-enantiomers and the R-enantiomers as wellas mixtures of these enantiomers, in particular racemic mixtures andalso pure diastereomers and mixtures of said diastereomers.

TABLE A # R¹ R³ R⁵ [CR^(4a)R^(4b)]_(m) 1. H H H — 2. H CH₃ CH₃ — 3. HCH₂CH₃ CH₂CH₃ — 4. H F F — 5. H Cl Cl — 6. H H F — 7. H H Cl — 8. H H Br— 9. H CH₃ F — 10. H CH₃ Cl — 11. H CH₃ Br — 12. H H CH₃ — 13. H HCH₂CH₃ — 14. H H CH₂CH₂CH₃ — 15. H H CH(CH₃)₂ — 16. H H CH₂CH₂CH₂CH₃ —17. H H CH(CH₃)CH₂CH₃ — 18. H H CH₂CH(CH₃)₂ — 19. H H CN — 20. H Hc-C₃H₅ — 21. H H c-C₄H₇ — 22. H H c-C₅H₉ — 23. H H c-C₆H₁₁ — 24. H HC₆H₅ — 25. H H 4-Cl—C₆H₄ — 26. H H 4-F—C₆H₄ — 27. H H 4-Br—C₆H₄ — 28. HH 3-Cl—C₆H₄ — 29. H H 3-F—C₆H₄ — 30. H H 3-Br—C₆H₄ — 31. H H 2-Cl—C₆H₄ —32. H H 2-F—C₆H₄ — 33. H H 2-Br—C₆H₄ — 34. H H 2-CN—C₆H₄ — 35. H H3-CN—C₆H₄ — 36. H H 4-CN—C₆H₄ — 37. H H 3-CH₃O—C₆H₄ — 38. H H4-CH₃—O—C₆H₄ — 39. H H 3,4-(CH₃O)₂—C₆H₃ — 40. H H 3,4,5-(CH₃O)₃—C₆H₂ —41. H H 3-CH₃O-4-F—C₆H₃ — 42. H H 4-CH₃O-3-F—C₆H₃ — 43. H H 2-CH₃—C₆H₄ —44. H H 3-CH₃—C₆H₄ — 45. H H 4-CH₃—C₆H₄ — 46. H H 2-CF₃—C₆H₄ — 47. H H3-CF₃—C₆H₄ — 48. H H 4-CF₃—C₆H₄ — 49. H H 3,4-Cl₂—C₆H₃ — 50. H H2,3-Cl₂—C₆H₃ — 51. H H 3,5-Cl₂—C₆H₃ — 52. H H 2,4-Cl₂—C₆H₃ — 53. H H2,5-Cl₂—C₆H₃ — 54. H H 2,6-Cl₂—C₆H₃ — 55. H H 3,4-F₂—C₆H₃ — 56. H H3,5-F₂—C₆H₃ — 57. H H 2,3-F₂—C₆H₃ — 58. H H 2,4-F₂—C₆H₃ — 59. H H2,5-F₂—C₆H₃ — 60. H H 2,6-F₂—C₆H₃ — 61. H H 3-Cl-4-F—C₆H₃ — 62. H H4-Cl-3-F—C₆H₃ — 63. H H 3-Br-4-F—C₆H₃ — 64. H H 4-Br-3-F—C₆H₃ — 65. H H3-Br-4-Cl—C₆H₃ — 66. H H 4-Br-3-Cl—C₆H₃ — 67. H H 2-Cl-5-NO₂—C₆H₃ — 68.H CH₃ CH₂CH₃ — 69. H CH₃ CH₂CH₂CH₃ — 70. H CH₃ CH(CH₃)₂ — 71. H CH₃CH₂CH₂CH₂CH₃ — 72. H CH₃ CH(CH₃)CH₂CH₃ — 73. H CH₃ CH₂CH(CH₃)₂ — 74. HCH₃ CN — 75. H CH₃ c-C₃H₅ — 76. H CH₃ c-C₄H₇ — 77. H CH₃ c-C₅H₉ — 78. HCH₃ c-C₆H₁₁ — 79. H CH₃ C₆H₅ — 80. H CH₃ 4-Cl—C₆H₄ — 81. H CH₃ 4-F—C₆H₄— 82. H CH₃ 4-Br—C₆H₄ — 83. H CH₃ 3-Cl—C₆H₄ — 84. H CH₃ 3-F—C₆H₄ — 85. HCH₃ 3-Br—C₆H₄ — 86. H CH₃ 2-Cl—C₆H₄ — 87. H CH₃ 2-F—C₆H₄ — 88. H CH₃2-Br—C₆H₄ — 89. H CH₃ 2-CN—C₆H₄ — 90. H CH₃ 3-CN—C₆H₄ — 91. H CH₃4-CN—C₆H₄ — 92. H CH₃ 3-CH₃O—C₆H₄ — 93. H CH₃ 4-CH₃—O—C₆H₄ — 94. H CH₃3,4-(CH₃O)₂—C₆H₃ — 95. H CH₃ 3,4,5-(CH₃O)₃—C₆H₂ — 96. H CH₃3-CH₃O-4-F—C₆H₃ — 97. H CH₃ 4-CH₃O-3-F—C₆H₃ — 98. H CH₃ 2-CH₃—C₆H₄ — 99.H CH₃ 3-CH₃—C₆H₄ — 100. H CH₃ 4-CH₃—C₆H₄ — 101. H CH₃ 2-CF₃—C₆H₄ — 102.H CH₃ 3-CF₃—C₆H₄ — 103. H CH₃ 4-CF₃—C₆H₄ — 104. H CH₃ 3,4-Cl₂—C₆H₃ —105. H CH₃ 2,3-Cl₂—C₆H₃ — 106. H CH₃ 3,5-Cl₂—C₆H₃ — 107. H CH₃2,4-Cl₂—C₆H₃ — 108. H CH₃ 2,5-Cl₂—C₆H₃ — 109. H CH₃ 2,6-Cl₂—C₆H₃ — 110.H CH₃ 3,4-F₂—C₆H₃ — 111. H CH₃ 3,5-F₂—C₆H₃ — 112. H CH₃ 2,3-F₂—C₆H₃ —113. H CH₃ 2,4-F₂—C₆H₃ — 114. H CH₃ 2,5-F₂—C₆H₃ — 115. H CH₃ 2,6-F₂—C₆H₃— 116. H CH₃ 3-Cl-4-F—C₆H₃ — 117. H CH₃ 4-Cl-3-F—C₆H₃ — 118. H CH₃3-Br-4-F—C₆H₃ — 119. H CH₃ 4-Br-3-F—C₆H₃ — 120. H CH₃ 3-Br-4-Cl—C₆H₃ —121. H CH₃ 4-Br-3-Cl—C₆H₃ — 122. H C₂H₅ C₆H₅ — 123. H C₂H₅ 4-Cl—C₆H₄ —124. H C₂H₅ 4-F—C₆H₄ — 125. H C₂H₅ 4-Br—C₆H₄ — 126. H C₂H₅ 3-Cl—C₆H₄ —127. H C₂H₅ 3-F—C₆H₄ — 128. H C₂H₅ 3-Br—C₆H₄ — 129. H C₂H₅ 2-Cl—C₆H₄ —130. H C₂H₅ 2-F—C₆H₄ — 131. H C₂H₅ 2-Br—C₆H₄ — 132. H C₂H₅ 2-CN—C₆H₄ —133. H C₂H₅ 3-CN—C₆H₄ — 134. H C₂H₅ 4-CN—C₆H₄ — 135. H C₂H₅ 3-CH₃O—C₆H₄— 136. H C₂H₅ 4-CH₃—O—C₆H₄ — 137. H C₂H₅ 3,4-(CH₃O)₂—C₆H₃ — 138. H C₂H₅3,4,5-(CH₃O)₃—C₆H₂ — 139. H C₂H₅ 3-CH₃O-4-F—C₆H₃ — 140. H C₂H₅4-CH₃O-3-F—C₆H₃ — 141. H C₂H₅ 2-CH₃—C₆H₄ — 142. H C₂H₅ 3-CH₃—C₆H₄ — 143.H C₂H₅ 4-CH₃—C₆H₄ — 144. H C₂H₅ 2-CF₃—C₆H₄ — 145. H C₂H₅ 3-CF₃—C₆H₄ —146. H C₂H₅ 4-CF₃—C₆H₄ — 147. H C₂H₅ 3,4-Cl₂—C₆H₃ — 148. H C₂H₅2,3-Cl₂—C₆H₃ — 149. H C₂H₅ 3,5-Cl₂—C₆H₃ — 150. H C₂H₅ 2,4-Cl₂—C₆H₃ —151. H C₂H₅ 2,5-Cl₂—C₆H₃ — 152. H C₂H₅ 2,6-Cl₂—C₆H₃ — 153. H C₂H₅3,4-F₂—C₆H₃ — 154. H C₂H₅ 3,5-F₂—C₆H₃ — 155. H C₂H₅ 2,3-F₂—C₆H₃ — 156. HC₂H₅ 2,4-F₂—C₆H₃ — 157. H C₂H₅ 2,5-F₂—C₆H₃ — 158. H C₂H₅ 2,6-F₂—C₆H₃ —159. H C₂H₅ 3-Cl-4-F—C₆H₃ — 160. H C₂H₅ 4-Cl-3-F—C₆H₃ — 161. H C₂H₅3-Br-4-F—C₆H₃ — 162. H C₂H₅ 4-Br-3-F—C₆H₃ — 163. H C₂H₅ 3-Br-4-Cl—C₆H₃ —164. H C₂H₅ 4-Br-3-Cl—C₆H₃ — 165. H CH₂CH═CH₂ CH₂CH═CH₂ — 166. HCH₂C(CH₃)═CH₂ CH₂C(CH₃)═CH₂ — 167. H (CH₃)₂C═CHCH₂ (CH₃)₂C═CHCH₂ — 168.H H (CH₃)₂C═CHCH₂ — 169. H H CH₂CH═CH₂ — 170. H H c-C₃H₅ CH₂ 171. H Hc-C₄H₇ CH₂ 172. H H c-C₅H₉ CH₂ 173. H H c-C₆H₁₁ CH₂ 174. H H C₆H₅ CH₂175. H H 4-Cl—C₆H₄ CH₂ 176. H H 4-F—C₆H₄ CH₂ 177. H H 4-Br—C₆H₄ CH₂ 178.H H 3-Cl—C₆H₄ CH₂ 179. H H 3-F—C₆H₄ CH₂ 180. H H 3-Br—C₆H₄ CH₂ 181. H H2-Cl—C₆H₄ CH₂ 182. H H 2-F—C₆H₄ CH₂ 183. H H 2-Br—C₆H₄ CH₂ 184. H H2-CN—C₆H₄ CH₂ 185. H H 3-CN—C₆H₄ CH₂ 186. H H 4-CN—C₆H₄ CH₂ 187. H H3-CH₃O—C₆H₄ CH₂ 188. H H 4-CH₃—O—C₆H₄ CH₂ 189. H H 3,4-(CH₃O)₂—C₆H₃ CH₂190. H H 3,4,5-(CH₃O)₃—C₆H₂ CH₂ 191. H H 3-CH₃O-4-F—C₆H₃ CH₂ 192. H H4-CH₃O-3-F—C₆H₃ CH₂ 193. H H 2-CH₃—C₆H₄ CH₂ 194. H H 3-CH₃—C₆H₄ CH₂ 195.H H 4-CH₃—C₆H₄ CH₂ 196. H H 2-CF₃—C₆H₄ CH₂ 197. H H 3-CF₃—C₆H₄ CH₂ 198.H H 4-CF₃—C₆H₄ CH₂ 199. H H 3,4-Cl₂—C₆H₃ CH₂ 200. H H 2,3-Cl₂—C₆H₃ CH₂201. H H 3,5-Cl₂—C₆H₃ CH₂ 202. H H 2,4-Cl₂—C₆H₃ CH₂ 203. H H2,5-Cl₂—C₆H₃ CH₂ 204. H H 2,6-Cl₂—C₆H₃ CH₂ 205. H H 3,4-F₂—C₆H₃ CH₂ 206.H H 3,5-F₂—C₆H₃ CH₂ 207. H H 2,3-F₂—C₆H₃ CH₂ 208. H H 2,4-F₂—C₆H₃ CH₂209. H H 2,5-F₂—C₆H₃ CH₂ 210. H H 2,6-F₂—C₆H₃ CH₂ 211. H H 3-Cl-4-F—C₆H₃CH₂ 212. H H 4-Cl-3-F—C₆H₃ CH₂ 213. H H 3-Br-4-F—C₆H₃ CH₂ 214. H H4-Br-3-F—C₆H₃ CH₂ 215. H H 3-Br-4-Cl—C₆H₃ CH₂ 216. H H 4-Br-3-Cl—C₆H₃CH₂ 217. H H 2-Cl-5-NO₂—C₆H₃ CH₂ 218. H H 2-methyl-1,3- CH₂dioxolan-2-yl 219. H H c-C₃H₅ C═O 220. H H c-C₄H₇ C═O 221. H H c-C₅H₉C═O 222. H H c-C₆H₁₁ C═O 223. H H C₆H₅ C═O 224. H H 4-Cl—C₆H₄ C═O 225. HH 4-F—C₆H₄ C═O 226. H H 4-Br—C₆H₄ C═O 227. H H 3-Cl—C₆H₄ C═O 228. H H3-F—C₆H₄ C═O 229. H H 3-Br—C₆H₄ C═O 230. H H 2-Cl—C₆H₄ C═O 231. H H2-F—C₆H₄ C═O 232. H H 2-Br—C₆H₄ C═O 233. H H 2-CN—C₆H₄ C═O 234. H H3-CN—C₆H₄ C═O 235. H H 4-CN—C₆H₄ C═O 236. H H 3-CH₃O—C₆H₄ C═O 237. H H4-CH₃—O—C₆H₄ C═O 238. H H 3,4-(CH₃O)₂—C₆H₃ C═O 239. H H3,4,5-(CH₃O)₃—C₆H₂ C═O 240. H H 3-CH₃O-4-F—C₆H₃ C═O 241. H H4-CH₃O-3-F—C₆H₃ C═O 242. H H 2-CH₃—C₆H₄ C═O 243. H H 3-CH₃—C₆H₄ C═O 244.H H 4-CH₃—C₆H₄ C═O 245. H H 2-CF₃—C₆H₄ C═O 246. H H 3-CF₃—C₆H₄ C═O 247.H H 4-CF₃—C₆H₄ C═O 248. H H 3,4-Cl₂—C₆H₃ C═O 249. H H 2,3-Cl₂—C₆H₃ C═O250. H H 3,5-Cl₂—C₆H₃ C═O 251. H H 2,4-Cl₂—C₆H₃ C═O 252. H H2,5-Cl₂—C₆H₃ C═O 253. H H 2,6-Cl₂—C₆H₃ C═O 254. H H 3,4-F₂—C₆H₃ C═O 255.H H 3,5-F₂—C₆H₃ C═O 256. H H 2,3-F₂—C₆H₃ C═O 257. H H 2,4-F₂—C₆H₃ C═O258. H H 2,5-F₂—C₆H₃ C═O 259. H H 2,6-F₂—C₆H₃ C═O 260. H H 3-Cl-4-F—C₆H₃C═O 261. H H 4-Cl-3-F—C₆H₃ C═O 262. H H 3-Br-4-F—C₆H₃ C═O 263. H H4-Br-3-F—C₆H₃ C═O 264. H H 3-Br-4-Cl—C₆H₃ C═O 265. H H 4-Br-3-Cl—C₆H₃C═O 266. H H C₆H₅ CH(CH₃) 267. H H 4-Cl—C₆H₄ CH(CH₃) 268. H H 4-F—C₆H₄CH(CH₃) 269. H H 4-Br—C₆H₄ CH(CH₃) 270. H H 3-Cl—C₆H₄ CH(CH₃) 271. H H3-F—C₆H₄ CH(CH₃) 272. H H 3-Br—C₆H₄ CH(CH₃) 273. H H 2-Cl—C₆H₄ CH(CH₃)274. H H 2-F—C₆H₄ CH(CH₃) 275. H H 2-Br—C₆H₄ CH(CH₃) 276. H H 2-CN—C₆H₄CH(CH₃) 277. H H 3-CN—C₆H₄ CH(CH₃) 278. H H 4-CN—C₆H₄ CH(CH₃) 279. H H3-CH₃O—C₆H₄ CH(CH₃) 280. H H 4-CH₃—O—C₆H₄ CH(CH₃) 281. H H3,4-(CH₃O)₂—C₆H₃ CH(CH₃) 282. H H 3,4,5-(CH₃O)₃—C₆H₂ CH(CH₃) 283. H H3-CH₃O-4-F—C₆H₃ CH(CH₃) 284. H H 4-CH₃O-3-F—C₆H₃ CH(CH₃) 285. H H2-CH₃—C₆H₄ CH(CH₃) 286. H H 3-CH₃—C₆H₄ CH(CH₃) 287. H H 4-CH₃—C₆H₄CH(CH₃) 288. H H 2-CF₃—C₆H₄ CH(CH₃) 289. H H 3-CF₃—C₆H₄ CH(CH₃) 290. H H4-CF₃—C₆H₄ CH(CH₃) 291. H H 3,4-Cl₂—C₆H₃ CH(CH₃) 292. H H 2,3-Cl₂—C₆H₃CH(CH₃) 293. H H 3,5-Cl₂—C₆H₃ CH(CH₃) 294. H H 2,4-Cl₂—C₆H₃ CH(CH₃) 295.H H 2,5-Cl₂—C₆H₃ CH(CH₃) 296. H H 2,6-Cl₂—C₆H₃ CH(CH₃) 297. H H3,4-F₂—C₆H₃ CH(CH₃) 298. H H 3,5-F₂—C₆H₃ CH(CH₃) 299. H H 2,3-F₂—C₆H₃CH(CH₃) 300. H H 2,4-F₂—C₆H₃ CH(CH₃) 301. H H 2,5-F₂—C₆H₃ CH(CH₃) 302. HH 2,6-F₂—C₆H₃ CH(CH₃) 303. H H 3-Cl-4-F—C₆H₃ CH(CH₃) 304. H H4-Cl-3-F—C₆H₃ CH(CH₃) 305. H H 3-Br-4-F—C₆H₃ CH(CH₃) 306. H H4-Br-3-F—C₆H₃ CH(CH₃) 307. H H 3-Br-4-Cl—C₆H₃ CH(CH₃) 308. H H4-Br-3-Cl—C₆H₃ CH(CH₃) 309. H CH₂—CH₂ — 310. H CHF—CHF — 311. H CF₂—CF₂— 312. H CHCl—CHCl — 313. H CCl₂—CCl₂ — 314. H CH(CH₃)—CH(CH₃) — 315. HC(CH₃)₂—C(CH₃)₂ — 316. H CH₂—CH₂—CH₂ — 317. H CH₂—CHF—CH₂ — 318. HCHF—CH₂—CHF — 319. H CHF—CHF—CHF — 320. H CH₂—CF₂—CH₂ — 321. HCH₂—CHCl—CH₂ — 322. H CH₂—CCl₂—CH₂ — 323. H CHCl—CH₂—CHCl — 324. HCHCl—CHCl—CHCl — 325. H CCl₂—CH₂—CCl₂ — 326. H CCl₂—CCl₂—CCl₂ — 327. HCH(CH₃)—CH₂—CH(CH₃) — 328. H CH(CH₃)—CH(CH₃)—CH(CH₃) — 329. HC(CH₃)₂—CH₂—C(CH₃)₂ — 330. H C(CH₃)₂—C(CH₃)₂—C(CH₃)₂ — 331. HCH₂—CH(CH₃)—CH₂ — 332. H CH₂—C(CH₃)₂—CH₂ — 333. H CHF—CH₂ — 334. HCF₂—CH₂ — 335. H CF₂—CHF — 336. H CHCl—CH₂ — 337. H CCl₂—CH₂ — 338. HCCl₂—CHCl — 339. H CH(CH₃)—CH₂ — 340. H C(CH₃)₂—CH₂ — 341. HC(CH₃)₂—CH(CH₃) — 342. H CH(OCH₃)—CH₂ — 343. H CH(CH₂CH₃)—CH₂ — 344. HCH(CH₂CH₂CH₃)—CH₂ — 345. H CH(CH₂CH₂CH₂CH₃)—CH₂ — 346. H CH(C₆H₅)—CH₂ —347. H CH(2-Cl—C₆H₄)—CH₂ — 348. H CH(2-F—C₆H₄)—CH₂ — 349. HCH(2-CN—C₆H₄)—CH₂ — 350. H CH(2-CH₃—C₆H₄)—CH₂ — 351. HCH(2-OCH₃—C₆H₄)—CH₂ — 352. H CH(3-Cl—C₆H₄)—CH₂ — 353. H CH(3-F—C₆H₄)—CH₂— 354. H CH(3-CN—C₆H₄)—CH₂ — 355. H CH(3-CH₃—C₆H₄)—CH₂ — 356. HCH(3-OCH₃—C₆H₄)—CH₂ — 357. H CH(4-Cl—C₆H₄)—CH₂ — 358. H CH(4-F—C₆H₄)—CH₂— 359. H CH(4-CN—C₆H₄)—CH₂ — 360. H CH(4-CH₃—C₆H₄)—CH₂ — 361. HCH(4-OCH₃—C₆H₄)—CH₂ — 362. H CH(CH₃)—CH₂—CH₂ — 363. H C(CH₃)₂—CH₂—CH₂ —364. H CH(CH₃)—CH(CH₃)—CH₂ — 365. H C(CH₃)₂—CH(CH₃)—CH₂ — 366. HCH(CH₃)—C(CH₃)₂—CH₂ — 367. H C(CH₃)₂—C(CH₃)₂—CH₂ — 368. H CHF—CH₂—CH₂ —369. H CF₂—CH₂—CH₂ — 370. H CHF—CHF—CH₂ — 371. H CF₂—CHF—CH₂ — 372. HCHF—CF₂—CH₂ — 373. H CF₂—CH₂—CF₂ — 374. H CF₂—CF₂—CH₂ — 375. HCF₂—CF₂—CF₂ — 376. H CHCl—CH₂—CH₂ — 377. H CCl₂—CH₂—CH₂ — 378. HCHCl—CHCl—CH₂ — 379. H CCl₂—CHCl—CH₂ — 380. H CHCl—CCl₂—CH₂ — 381. HCCl₂—CCl₂—CH₂ — 382. H CH₂CH═CHCH₂ — 383. H CH₂OCH₂ — 384. HCH₂CH₂CH₂CH₂ — 385. H OCH₂ — 386. H OCH₂CH₂ — 387. H CH₂OCH₂ — 388. HCH(CH(CH₃)₂)—CH₂ — 389. H CH(c-C₃H₅)—CH₂ — 390. H CH(c-C₅H₇)—CH₂ — 391.H CH(c-C₆H₁₁)—CH₂ — 392. H CH(c-C₇H₁₃)—CH₂ — 393. H CH(c-C₈H₁₅)—CH₂ —394. H CH(CH(CH₃)CH₂CH₂CH₃)—CH₂ — 395. H CH(CH₂C(CH₃)₃)—CH₂ — 396. HCH(CH₂CH(CH₃)₂)—CH₂ — 397. H CH(CH₂CH₂C₆H₅)—CH₂ — 398. HCH(CH(CH₃)CH(CH₃)CH₂CH₃)—CH₂ — 399. H CH(CH₂CH₂CH₂CH₂CH₃)—CH₂ — 400. HCH(CH₂CH₂C(CH₃)₃)—CH₂ — 401. H CH(4-THP)-CH₂ — 402. HCH(CH(C₂H₅)CH₂CH₂CH₂CH₃)—CH₂ — 403. H CH(C(CH₃)₃)—CH₂ — 404. HCH(non-3-enyl)-CH₂ — 405. H CH(C(CH₃)₂CH₂-3-Py)—CH₂ — 406. H CH(CF₃)—CH₂— 407. H 6,6-DM-2-N 408. H CH(3-THTP)-CH₂ — 409. H CH(1-AOE)-CH₂ — 410.H CH(CH(CH₃)OCH(CH₃)₂)—CH₂ — 411. H CH(CH(CH₃)CH₂SCH₃)—CH₂ 412. HCH(CH₂CH₂OCH₂CH₂CH₃)—CH₂ — 413. H CH(2-Me—c-C₆H₈)—CH₂ — 414. HCH(4-Me—c-C₆H₁₀)—CH₂ — 415. H CH(5,5-DM-2-THF)—CH₂ — 416. HCH(CH₂-4-THP)-CH₂ — 417. H CH(CH₂CH₂OCH₂CH(CH₃)₂)—CH₂ — 418. HCH(CH(CH₃)OCH₂CH₂OCH₃)—CH₂ — 419. H CH(2-EC-c-C₃H₅)—CH₂ 420. HCH(CH(CH₃)OCH₃)—CH₂ — 421. H CH(CH(CH₃)CH(CH₃)₂)—CH₂ — 422. HCH(4-Me-5-TZ)-CH₂ — 423. H CH(3-THP)-CH₂ — 424. H CH(CH₂-4-THTP)-CH₂ —425. H CH(CH(CH₃)OC₆H₅)—CH₂ — 426. H CH(CH(CH₃)O—c-C₆H₁₁)—CH₂ — 427. HCH(4-Ip-c-C₆H₁₀)—CH₂ — 428. H CH(6-Ac—O—C₆H₁₂)—CH₂ — 429. HCH(3-CF₃—C₆H₄)—CH₂ — 430. H CH(3-NO₂—C₆H₄)—CH₂ — 431. H CH(2-Py)—CH₂ —432. H CH(4-CF₃—C₆H₄)—CH₂ — 433. H CH(CH₃—O—C(O))—CH₂ — 434. HCH(Bz)-CH₂ — 435. H CH(CH₂CF₃)—CH₂ — 436. H CH(3-THF)—CH₂ — 437. CH₃ H H— 438. CH₃ CH₃ CH₃ — 439. CH₃ CH₂CH₃ CH₂CH₃ — 440. CH₃ F F — 441. CH₃ ClCl — 442. CH₃ H F — 443. CH₃ H Cl — 444. CH₃ H Br — 445. CH₃ CH₃ F —446. CH₃ CH₃ Cl — 447. CH₃ CH₃ Br — 448. CH₃ H CH₃ — 449. CH₃ H CH₂CH₃ —450. CH₃ H CH₂CH₂CH₃ — 451. CH₃ H CH(CH₃)₂ — 452. CH₃ H CH₂CH₂CH₂CH₃ —453. CH₃ H CH(CH₃)CH₂CH₃ — 454. CH₃ H CH₂CH(CH₃)₂ — 455. CH₃ H CN — 456.CH₃ H c-C₃H₅ — 457. CH₃ H c-C₄H₇ — 458. CH₃ H c-C₅H₉ — 459. CH₃ Hc-C₆H₁₁ — 460. CH₃ H C₆H₅ — 461. CH₃ H 4-Cl—C₆H₄ — 462. CH₃ H 4-F—C₆H₄ —463. CH₃ H 4-Br—C₆H₄ — 464. CH₃ H 3-Cl—C₆H₄ — 465. CH₃ H 3-F—C₆H₄ — 466.CH₃ H 3-Br—C₆H₄ — 467. CH₃ H 2-Cl—C₆H₄ — 468. CH₃ H 2-F—C₆H₄ — 469. CH₃H 2-Br—C₆H₄ — 470. CH₃ H 2-CN—C₆H₄ — 471. CH₃ H 3-CN—C₆H₄ — 472. CH₃ H4-CN—C₆H₄ — 473. CH₃ H 3-CH₃O—C₆H₄ — 474. CH₃ H 4-CH₃—O—C₆H₄ — 475. CH₃H 3,4-(CH₃O)₂—C₆H₃ — 476. CH₃ H 3,4,5-(CH₃O)₃—C₆H₂ — 477. CH₃ H3-CH₃O-4-F—C₆H₃ — 478. CH₃ H 4-CH₃O-3-F—C₆H₃ — 479. CH₃ H 2-CH₃—C₆H₄ —480. CH₃ H 3-CH₃—C₆H₄ — 481. CH₃ H 4-CH₃—C₆H₄ — 482. CH₃ H 2-CF₃—C₆H₄ —483. CH₃ H 3-CF₃—C₆H₄ — 484. CH₃ H 4-CF₃—C₆H₄ — 485. CH₃ H 3,4-Cl₂—C₆H₃— 486. CH₃ H 2,3-Cl₂—C₆H₃ — 487. CH₃ H 3,5-Cl₂—C₆H₃ — 488. CH₃ H2,4-Cl₂—C₆H₃ — 489. CH₃ H 2,5-Cl₂—C₆H₃ — 490. CH₃ H 2,6-Cl₂—C₆H₃ — 491.CH₃ H 3,4-F₂—C₆H₃ — 492. CH₃ H 3,5-F₂—C₆H₃ — 493. CH₃ H 2,3-F₂—C₆H₃ —494. CH₃ H 2,4-F₂—C₆H₃ — 495. CH₃ H 2,5-F₂—C₆H₃ — 496. CH₃ H 2,6-F₂—C₆H₃— 497. CH₃ H 3-Cl-4-F—C₆H₃ — 498. CH₃ H 4-Cl-3-F—C₆H₃ — 499. CH₃ H3-Br-4-F—C₆H₃ — 500. CH₃ H 4-Br-3-F—C₆H₃ — 501. CH₃ H 3-Br-4-Cl—C₆H₃ —502. CH₃ H 4-Br-3-Cl—C₆H₃ — 503. CH₃ H 2-Cl-5-NO₂—C₆H₃ — 504. CH₃ CH₃CH₂CH₃ — 505. CH₃ CH₃ CH₂CH₂CH₃ — 506. CH₃ CH₃ CH(CH₃)₂ — 507. CH₃ CH₃CH₂CH₂CH₂CH₃ — 508. CH₃ CH₃ CH(CH₃)CH₂CH₃ — 509. CH₃ CH₃ CH₂CH(CH₃)₂ —510. CH₃ CH₃ CN — 511. CH₃ CH₃ c-C₃H₅ — 512. CH₃ CH₃ c-C₄H₇ — 513. CH₃CH₃ c-C₅H₉ — 514. CH₃ CH₃ c-C₆H₁₁ — 515. CH₃ CH₃ C₆H₅ — 516. CH₃ CH₃4-Cl—C₆H₄ — 517. CH₃ CH₃ 4-F—C₆H₄ — 518. CH₃ CH₃ 4-Br—C₆H₄ — 519. CH₃CH₃ 3-Cl—C₆H₄ — 520. CH₃ CH₃ 3-F—C₆H₄ — 521. CH₃ CH₃ 3-Br—C₆H₄ — 522.CH₃ CH₃ 2-Cl—C₆H₄ — 523. CH₃ CH₃ 2-F—C₆H₄ — 524. CH₃ CH₃ 2-Br—C₆H₄ —525. CH₃ CH₃ 2-CN—C₆H₄ — 526. CH₃ CH₃ 3-CN—C₆H₄ — 527. CH₃ CH₃ 4-CN—C₆H₄— 528. CH₃ CH₃ 3-CH₃O—C₆H₄ — 529. CH₃ CH₃ 4-CH₃—O—C₆H₄ — 530. CH₃ CH₃3,4-(CH₃O)₂—C₆H₃ — 531. CH₃ CH₃ 3,4,5-(CH₃O)₃—C₆H₂ — 532. CH₃ CH₃3-CH₃O-4-F—C₆H₃ — 533. CH₃ CH₃ 4-CH₃O-3-F—C₆H₃ — 534. CH₃ CH₃ 2-CH₃—C₆H₄— 535. CH₃ CH₃ 3-CH₃—C₆H₄ — 536. CH₃ CH₃ 4-CH₃—C₆H₄ — 537. CH₃ CH₃2-CF₃—C₆H₄ — 538. CH₃ CH₃ 3-CF₃—C₆H₄ — 539. CH₃ CH₃ 4-CF₃—C₆H₄ — 540.CH₃ CH₃ 3,4-Cl₂—C₆H₃ — 541. CH₃ CH₃ 2,3-Cl₂—C₆H₃ — 542. CH₃ CH₃3,5-Cl₂—C₆H₃ — 543. CH₃ CH₃ 2,4-Cl₂—C₆H₃ — 544. CH₃ CH₃ 2,5-Cl₂—C₆H₃ —545. CH₃ CH₃ 2,6-Cl₂—C₆H₃ — 546. CH₃ CH₃ 3,4-F₂—C₆H₃ — 547. CH₃ CH₃3,5-F₂—C₆H₃ — 548. CH₃ CH₃ 2,3-F₂—C₆H₃ — 549. CH₃ CH₃ 2,4-F₂—C₆H₃ — 550.CH₃ CH₃ 2,5-F₂—C₆H₃ — 551. CH₃ CH₃ 2,6-F₂—C₆H₃ — 552. CH₃ CH₃3-Cl-4-F—C₆H₃ — 553. CH₃ CH₃ 4-Cl-3-F—C₆H₃ — 554. CH₃ CH₃ 3-Br-4-F—C₆H₃— 555. CH₃ CH₃ 4-Br-3-F—C₆H₃ — 556. CH₃ CH₃ 3-Br-4-Cl—C₆H₃ — 557. CH₃CH₃ 4-Br-3-Cl—C₆H₃ — 558. CH₃ C₂H₅ C₆H₅ — 559. CH₃ C₂H₅ 4-Cl—C₆H₄ — 560.CH₃ C₂H₅ 4-F—C₆H₄ — 561. CH₃ C₂H₆ 4-Br—C₆H₄ — 562. CH₃ C₂H₅ 3-Cl—C₆H₄ —563. CH₃ C₂H₅ 3-F—C₆H₄ — 564. CH₃ C₂H₅ 3-Br—C₆H₄ — 565. CH₃ C₂H₅2-Cl—C₆H₄ — 566. CH₃ C₂H₅ 2-F—C₆H₄ — 567. CH₃ C₂H₅ 2-Br—C₆H₄ — 568. CH₃C₂H₅ 2-CN—C₆H₄ — 569. CH₃ C₂H₅ 3-CN—C₆H₄ — 570. CH₃ C₂H₅ 4-CN—C₆H₄ —571. CH₃ C₂H₅ 3-CH₃O—C₆H₄ — 572. CH₃ C₂H₅ 4-CH₃—O—C₆H₄ — 573. CH₃ C₂H₅3,4-(CH₃O)₂—C₆H₃ — 574. CH₃ C₂H₅ 3,4,5-(CH₃O)₃—C₆H₂ — 575. CH₃ C₂H₅3-CH₃O-4-F—C₆H₃ — 576. CH₃ C₂H₅ 4-CH₃O-3-F—C₆H₃ — 577. CH₃ C₂H₅2-CH₃—C₆H₄ — 578. CH₃ C₂H₅ 3-CH₃—C₆H₄ — 579. CH₃ C₂H₅ 4-CH₃—C₆H₄ — 580.CH₃ C₂H₅ 2-CF₃—C₆H₄ — 581. CH₃ C₂H₅ 3-CF₃—C₆H₄ — 582. CH₃ C₂H₅4-CF₃—C₆H₄ — 583. CH₃ C₂H₅ 3,4-Cl₂—C₆H₃ — 584. CH₃ C₂H₅ 2,3-Cl₂—C₆H₃ —585. CH₃ C₂H₅ 3,5-Cl₂—C₆H₃ — 586. CH₃ C₂H₅ 2,4-Cl₂—C₆H₃ — 587. CH₃ C₂H₅2,5-Cl₂—C₆H₃ — 588. CH₃ C₂H₅ 2,6-Cl₂—C₆H₃ — 589. CH₃ C₂H₅ 3,4-F₂—C₆H₃ —590. CH₃ C₂H₅ 3,5-F₂—C₆H₃ — 591. CH₃ C₂H₅ 2,3-F₂—C₆H₃ — 592. CH₃ C₂H₅2,4-F₂—C₆H₃ — 593. CH₃ C₂H₅ 2,5-F₂—C₆H₃ — 594. CH₃ C₂H₅ 2,6-F₂—C₆H₃ —595. CH₃ C₂H₅ 3-Cl-4-F—C₆H₃ — 596. CH₃ C₂H₅ 4-Cl-3-F—C₆H₃ — 597. CH₃C₂H₅ 3-Br-4-F—C₆H₃ — 598. CH₃ C₂H₅ 4-Br-3-F—C₆H₃ — 599. CH₃ C₂H₅3-Br-4-Cl—C₆H₃ — 600. CH₃ C₂H₅ 4-Br-3-Cl—C₆H₃ — 601. CH₃ H CH₂CHCH₂ —602. CH₃ CH₂CH═CH₂ CH₂CH═CH₂ — 603. CH₃ CH₂C(CH₃)═CH₂ CH₂C(CH₃)═CH₂ —604. CH₃ H (CH₃)₂C═CHCH₂ — 605. CH₃ (CH₃)₂C═CHCH₂ (CH₃)₂C═CHCH₂ — 606.CH₃ H c-C₃H₅ CH₂ 607. CH₃ H c-C₄H₇ CH₂ 608. CH₃ H c-C₅H₉ CH₂ 609. CH₃ Hc-C₆H₁₁ CH₂ 610. CH₃ H C₆H₅ CH₂ 611. CH₃ H 4-Cl—C₆H₄ CH₂ 612. CH₃ H4-F—C₆H₄ CH₂ 613. CH₃ H 4-Br—C₆H₄ CH₂ 614. CH₃ H 3-Cl—C₆H₄ CH₂ 615. CH₃H 3-F—C₆H₄ CH₂ 616. CH₃ H 3-Br—C₆H₄ CH₂ 617. CH₃ H 2-Cl—C₆H₄ CH₂ 618.CH₃ H 2-F—C₆H₄ CH₂ 619. CH₃ H 2-Br—C₆H₄ CH₂ 620. CH₃ H 2-CN—C₆H₄ CH₂621. CH₃ H 3-CN—C₆H₄ CH₂ 622. CH₃ H 4-CN—C₆H₄ CH₂ 623. CH₃ H 3-CH₃O—C₆H₄CH₂ 624. CH₃ H 4-CH₃—O—C₆H₄ CH₂ 625. CH₃ H 3,4-(CH₃O)₂—C₆H₃ CH₂ 626. CH₃H 3,4,5-(CH₃O)₃—C₆H₂ CH₂ 627. CH₃ H 3-CH₃O-4-F—C₆H₃ CH₂ 628. CH₃ H4-CH₃O-3-F—C₆H₃ CH₂ 629. CH₃ H 2-CH₃—C₆H₄ CH₂ 630. CH₃ H 3-CH₃—C₆H₄ CH₂631. CH₃ H 4-CH₃—C₆H₄ CH₂ 632. CH₃ H 2-CF₃—C₆H₄ CH₂ 633. CH₃ H3-CF₃—C₆H₄ CH₂ 634. CH₃ H 4-CF₃—C₆H₄ CH₂ 635. CH₃ H 3,4-Cl₂—C₆H₃ CH₂636. CH₃ H 2,3-Cl₂—C₆H₃ CH₂ 637. CH₃ H 3,5-Cl₂—C₆H₃ CH₂ 638. CH₃ H2,4-Cl₂—C₆H₃ CH₂ 639. CH₃ H 2,5-Cl₂—C₆H₃ CH₂ 640. CH₃ H 2,6-Cl₂—C₆H₃ CH₂641. CH₃ H 3,4-F₂—C₆H₃ CH₂ 642. CH₃ H 3,5-F₂—C₆H₃ CH₂ 643. CH₃ H2,3-F₂—C₆H₃ CH₂ 644. CH₃ H 2,4-F₂—C₆H₃ CH₂ 645. CH₃ H 2,5-F₂—C₆H₃ CH₂646. CH₃ H 2,6-F₂—C₆H₃ CH₂ 647. CH₃ H 3-Cl-4-F—C₆H₃ CH₂ 648. CH₃ H4-Cl-3-F—C₆H₃ CH₂ 649. CH₃ H 3-Br-4-F—C₆H₃ CH₂ 650. CH₃ H 4-Br-3-F—C₆H₃CH₂ 651. CH₃ H 3-Br-4-Cl—C₆H₃ CH₂ 652. CH₃ H 4-Br-3-Cl—C₆H₃ CH₂ 653. CH₃H 2-Cl-5-NO₂—C₆H₃ CH₂ 654. CH₃ H 2-methyl-1,3- CH₂ dioxolan-2-yl 655.CH₃ H c-C₃H₅ C═O 656. CH₃ H c-C₄H₇ C═O 657. CH₃ H c-C₅H₉ C═O 658. CH₃ Hc-C₆H₁₁ C═O 659. CH₃ H C₆H₅ C═O 660. CH₃ H 4-Cl—C₆H₄ C═O 661. CH₃ H4-F—C₆H₄ C═O 662. CH₃ H 4-Br—C₆H₄ C═O 663. CH₃ H 3-Cl—C₆H₄ C═O 664. CH₃H 3-F—C₆H₄ C═O 665. CH₃ H 3-Br—C₆H₄ C═O 666. CH₃ H 2-Cl—C₆H₄ C═O 667.CH₃ H 2-F—C₆H₄ C═O 668. CH₃ H 2-Br—C₆H₄ C═O 669. CH₃ H 2-CN—C₆H₄ C═O670. CH₃ H 3-CN—C₆H₄ C═O 671. CH₃ H 4-CN—C₆H₄ C═O 672. CH₃ H 3-CH₃O—C₆H₄C═O 673. CH₃ H 4-CH₃—O—C₆H₄ C═O 674. CH₃ H 3,4-(CH₃O)₂—C₆H₃ C═O 675. CH₃H 3,4,5-(CH₃O)₃—C₆H₂ C═O 676. CH₃ H 3-CH₃O-4-F—C₆H₃ C═O 677. CH₃ H4-CH₃O-3-F—C₆H₃ C═O 678. CH₃ H 2-CH₃—C₆H₄ C═O 679. CH₃ H 3-CH₃—C₆H₄ C═O680. CH₃ H 4-CH₃—C₆H₄ C═O 681. CH₃ H 2-CF₃—C₆H₄ C═O 682. CH₃ H3-CF₃—C₆H₄ C═O 683. CH₃ H 4-CF₃—C₆H₄ C═O 684. CH₃ H 3,4-Cl₂—C₆H₃ C═O685. CH₃ H 2,3-Cl₂—C₆H₃ C═O 686. CH₃ H 3,5-Cl₂—C₆H₃ C═O 687. CH₃ H2,4-Cl₂—C₆H₃ C═O 688. CH₃ H 2,5-Cl₂—C₆H₃ C═O 689. CH₃ H 2,6-Cl₂—C₆H₃ C═O690. CH₃ H 3,4-F₂—C₆H₃ C═O 691. CH₃ H 3,5-F₂—C₆H₃ C═O 692. CH₃ H2,3-F₂—C₆H₃ C═O 693. CH₃ H 2,4-F₂—C₆H₃ C═O 694. CH₃ H 2,5-F₂—C₆H₃ C═O695. CH₃ H 2,6-F₂—C₆H₃ C═O 696. CH₃ H 3-Cl-4-F—C₆H₃ C═O 697. CH₃ H4-Cl-3-F—C₆H₃ C═O 698. CH₃ H 3-Br-4-F—C₆H₃ C═O 699. CH₃ H 4-Br-3-F—C₆H₃C═O 700. CH₃ H 3-Br-4-Cl—C₆H₃ C═O 701. CH₃ H 4-Br-3-Cl—C₆H₃ C═O 702. CH₃H C₆H₅ CH(CH₃) 703. CH₃ H 4-Cl—C₆H₄ CH(CH₃) 704. CH₃ H 4-F—C₆H₄ CH(CH₃)705. CH₃ H 4-Br—C₆H₄ CH(CH₃) 706. CH₃ H 3-Cl—C₆H₄ CH(CH₃) 707. CH₃ H3-F—C₆H₄ CH(CH₃) 708. CH₃ H 3-Br—C₆H₄ CH(CH₃) 709. CH₃ H 2-Cl—C₆H₄CH(CH₃) 710. CH₃ H 2-F—C₆H₄ CH(CH₃) 711. CH₃ H 2-Br—C₆H₄ CH(CH₃) 712.CH₃ H 2-CN—C₆H₄ CH(CH₃) 713. CH₃ H 3-CN—C₆H₄ CH(CH₃) 714. CH₃ H4-CN—C₆H₄ CH(CH₃) 715. CH₃ H 3-CH₃O—C₆H₄ CH(CH₃) 716. CH₃ H 4-CH₃—O—C₆H₄CH(CH₃) 717. CH₃ H 3,4-(CH₃O)₂—C₆H₃ CH(CH₃) 718. CH₃ H3,4,5-(CH₃O)₃—C₆H₂ CH(CH₃) 719. CH₃ H 3-CH₃O-4-F—C₆H₃ CH(CH₃) 720. CH₃ H4-CH₃O-3-F—C₆H₃ CH(CH₃) 721. CH₃ H 2-CH₃—C₆H₄ CH(CH₃) 722. CH₃ H3-CH₃—C₆H₄ CH(CH₃) 723. CH₃ H 4-CH₃—C₆H₄ CH(CH₃) 724. CH₃ H 2-CF₃—C₆H₄CH(CH₃) 725. CH₃ H 3-CF₃—C₆H₄ CH(CH₃) 726. CH₃ H 4-CF₃—C₆H₄ CH(CH₃) 727.CH₃ H 3,4-Cl₂—C₆H₃ CH(CH₃) 728. CH₃ H 2,3-Cl₂—C₆H₃ CH(CH₃) 729. CH₃ H3,5-Cl₂—C₆H₃ CH(CH₃) 730. CH₃ H 2,4-Cl₂—C₆H₃ CH(CH₃) 731. CH₃ H2,5-Cl₂—C₆H₃ CH(CH₃) 732. CH₃ H 2,6-Cl₂—C₆H₃ CH(CH₃) 733. CH₃ H3,4-F₂—C₆H₃ CH(CH₃) 734. CH₃ H 3,5-F₂—C₆H₃ CH(CH₃) 735. CH₃ H2,3-F₂—C₆H₃ CH(CH₃) 736. CH₃ H 2,4-F₂—C₆H₃ CH(CH₃) 737. CH₃ H2,5-F₂—C₆H₃ CH(CH₃) 738. CH₃ H 2,6-F₂—C₆H₃ CH(CH₃) 739. CH₃ H3-Cl-4-F—C₆H₃ CH(CH₃) 740. CH₃ H 4-Cl-3-F—C₆H₃ CH(CH₃) 741. CH₃ H3-Br-4-F—C₆H₃ CH(CH₃) 742. CH₃ H 4-Br-3-F—C₆H₃ CH(CH₃) 743. CH₃ H3-Br-4-Cl—C₆H₃ CH(CH₃) 744. CH₃ H 4-Br-3-Cl—C₆H₃ CH(CH₃) 745. CH₃CH₂—CH₂ — 746. CH₃ CHF—CHF — 747. CH₃ CF₂—CF₂ — 748. CH₃ CHCl—CHCl —749. CH₃ CCl₂—CCl₂ — 750. CH₃ CH(CH₃)—CH(CH₃) — 751. CH₃ C(CH₃)₂—C(CH₃)₂— 752. CH₃ CH₂—CH₂—CH₂ — 753. CH₃ CH₂—CHF—CH₂ — 754. CH₃ CHF—CH₂—CHF —755. CH₃ CHF—CHF—CHF — 756. CH₃ CH₂—CF₂—CH₂ — 757. CH₃ CH₂—CHCl—CH₂ —758. CH₃ CH₂—CCl₂—CH₂ — 759. CH₃ CHCl—CH₂—CHCl — 760. CH₃ CHCl—CHCl—CHCl— 761. CH₃ CCl₂—CH₂—CCl₂ — 762. CH₃ CCl₂—CCl₂—CCl₂ — 763. CH₃CH(CH₃)—CH₂—CH(CH₃) — 764. CH₃ CH(CH₃)—CH(CH₃)—CH(CH₃) — 765. CH₃C(CH₃)₂—CH₂—C(CH₃)₂ — 766. CH₃ C(CH₃)₂—C(CH₃)₂—C(CH₃)₂ — 767. CH₃CH₂—CH(CH₃)—CH₂ — 768. CH₃ CH₂—C(CH₃)₂—CH₂ — 769. CH₃ CHF—CH₂ — 770. CH₃CF₂—CH₂ — 771. CH₃ CF₂—CHF — 772. CH₃ CHCl—CH₂ — 773. CH₃ CCl₂—CH₂ —774. CH₃ CCl₂—CHCl — 775. CH₃ CH(CH₃)—CH₂ — 776. CH₃ C(CH₃)₂—CH₂ — 777.CH₃ C(CH₃)₂—CH(CH₃) — 778. CH₃ CH(OCH₃)—CH₂ — 779. CH₃ CH(CH₂CH₃)—CH₂ —780. CH₃ CH(CH₂CH₂CH₃)—CH₂ — 781. CH₃ CH(CH₂CH₂CH₂CH₃)—CH₂ — 782. CH₃CH(C₆H₅)—CH₂ — 783. CH₃ CH(2-Cl—C₆H₄)—CH₂ — 784. CH₃ CH(2-F—C₆H₄)—CH₂ —785. CH₃ CH(2-CN—C₆H₄)—CH₂ — 786. CH₃ CH(2-CH₃—C₆H₄)—CH₂ — 787. CH₃CH(2-OCH₃—C₆H₄)—CH₂ — 788. CH₃ CH(3-Cl—C₆H₄)—CH₂ — 789. CH₃CH(3-F—C₆H₄)—CH₂ — 790. CH₃ CH(3-CN—C₆H₄)—CH₂ — 791. CH₃CH(3-CH₃—C₆H₄)—CH₂ — 792. CH₃ CH(3-OCH₃—C₆H₄)—CH₂ — 793. CH₃CH(4-Cl—C₆H₄)—CH₂ — 794. CH₃ CH(4-F—C₆H₄)—CH₂ — 795. CH₃CH(4-CN—C₆H₄)—CH₂ — 796. CH₃ CH(4-CH₃—C₆H₄)—CH₂ — 797. CH₃CH(4-OCH₃—C₆H₄)—CH₂ — 798. CH₃ CH(CH₃)—CH₂—CH₂ — 799. CH₃C(CH₃)₂—CH₂—CH₂ — 800. CH₃ CH(CH₃)—CH(CH₃)—CH₂ — 801. CH₃C(CH₃)₂—CH(CH₃)—CH₂ — 802. CH₃ CH(CH₃)—C(CH₃)₂—CH₂ — 803. CH₃C(CH₃)₂—C(CH₃)₂—CH₂ — 804. CH₃ CHF—CH₂—CH₂ — 805. CH₃ CF₂—CH₂—CH₂ — 806.CH₃ CHF—CHF—CH₂ — 807. CH₃ CF₂—CHF—CH₂ — 808. CH₃ CHF—CF₂—CH₂ — 809. CH₃CF₂—CH₂—CF₂ — 810. CH₃ CF₂—CF₂—CH₂ — 811. CH₃ CF₂—CF₂—CF₂ — 812. CH₃CHCl—CH₂—CH₂ — 813. CH₃ CCl₂—CH₂—CH₂ — 814. CH₃ CHCl—CHCl—CH₂ — 815. CH₃CCl₂—CHCl—CH₂ — 816. CH₃ CHCl—CCl₂—CH₂ — 817. CH₃ CCl₂—CCl₂—CH₂ — 818.CH₃ CH₂CH═CHCH₂ — 819. CH₃ CH₂OCH₂ — 820. CH₃ CH₂CH₂CH₂CH₂ — 821. CH₃OCH₂ — 822. CH₃ OCH₂CH₂ — 823. CH₃ CH₂OCH₂ — 824. CH₃ CH(CH(CH₃)₂)—CH₂ —825. CH₃ CH(c-C₃H₅)—CH₂ — 826. CH₃ CH(c-C₅H₇)—CH₂ — 827. CH₃CH(c-C₆H₁₁)—CH₂ — 828. CH₃ CH(c-C₇H₁₃)—CH₂ — 829. CH₃ CH(c-C₈H₁₅)—CH₂ —830. CH₃ CH(CH(CH₃)CH₂CH₂CH₃)—CH₂ — 831. CH₃ CH(CH₂C(CH₃)₃)—CH₂ — 832.CH₃ CH(CH₂CH(CH₃)₂)—CH₂ — 833. CH₃ CH(CH₂CH₂C₆H₅)—CH₂ — 834. CH₃CH(CH(CH₃)CH(CH₃)CH₂CH₃)—CH₂ — 835. CH₃ CH(CH₂CH₂CH₂CH₂CH₃)—CH₂ — 836.CH₃ CH(CH₂CH₂C(CH₃)₃)—CH₂ — 837. CH₃ CH(4-THP)-CH₂ — 838. CH₃CH(CH(C₂H₅)CH₂CH₂CH₂CH₃)—CH₂ — 839. CH₃ CH(C(CH₃)₃)—CH₂ — 840. CH₃CH(non-3-enyl)-CH₂ — 841. CH₃ CH(C(CH₃)₂CH₂-3-Py)—CH₂ — 842. CH₃CH(CF₃)—CH₂ — 843. CH₃ 6,6-DM-2-N 844. CH₃ CH(3-THTP)-CH₂ — 845. CH₃CH(1-AOE)-CH₂ — 846. CH₃ CH(CH(CH₃)OCH(CH₃)₂)—CH₂ — 847. CH₃CH(CH(CH₃)CH₂SCH₃)—CH₂ 848. CH₃ CH(CH₂CH₂OCH₂CH₂CH₃)—CH₂ — 849. CH₃CH(2-Me—c-C₆H₈)—CH₂ — 850. CH₃ CH(4-Me—c-C₆H₁₀)—CH₂ — 851. CH₃CH(5,5-DM-2-THF)—CH₂ — 852. CH₃ CH(CH₂-4-THP)-CH₂ — 853. CH₃CH(CH₂CH₂OCH₂CH(CH₃)₂)—CH₂ — 854. CH₃ CH(CH(CH₃)OCH₂CH₂OCH₃)—CH₂ — 855.CH₃ CH(2-EC-c-C₃H₅)—CH₂ 856. CH₃ CH(CH(CH₃)OCH₃)—CH₂ — 857. CH₃CH(CH(CH₃)CH(CH₃)₂)—CH₂ — 858. CH₃ CH(4-Me-5-TZ)-CH₂ — 859. CH₃CH(3-THP)-CH₂ — 860. CH₃ CH(CH₂-4-THTP)-CH₂ — 861. CH₃CH(CH(CH₃)OC₆H₅)—CH₂ — 862. CH₃ CH(CH(CH₃)O—c-C₆H₁₁)—CH₂ — 863. CH₃CH(4-Ip-c-C₆H₁₀)—CH₂ — 864. CH₃ CH(6-Ac—O—C₆H₁₂)—CH₂ — 865. CH₃CH(3-CF₃—C₆H₄)—CH₂ — 866. CH₃ CH(3-NO₂—C₆H₄)—CH₂ — 867. CH₃ CH(2-Py)—CH₂— 868. CH₃ CH(4-CF₃—C₆H₄)—CH₂ — 869. CH₃ CH(CH₃—O—C(O))—CH₂ — 870. CH₃CH(Bz)-CH₂ — 871. CH₃ CH(CH₂CF₃)—CH₂ — 872. CH₃ CH(3-THF)—CH₂ —

In table A, the following abbreviations are used:

In the last column “-” indicates that m=0, i.e. [CR^(4a)R^(4b)] isabsent.

-   c-C₃H₅: cyclopropyl-   c-C₄H₇: cyclobutyl-   c-C₅H₉: cyclopentyl-   c-C₆H₁₁₁: cyclohexyl-   2-Me-c-C₆H₈: 2-methyl cyclohexen-3-yl-   4-Me-c-C₆H₁₀: 4-methylcyclohexyl-   c-C₇H₁₃: cycloheptyl-   c-C₈H₁₅: cyclooctyl-   C₆H₅: phenyl-   CH₂—C₆H₅: benzyl-   CH₂CH₂—C₆H₅: phenetyl-   2-Cl—C₆H₄: 2-chiorophenyl-   2-F—C₆H₄: 2-fluorophenyl-   2-Br—C₆H₄: 2-bromophenyl-   4-Cl—C₆H₄: 4-chiorophenyl-   4-F—C₆H₄: 4-fluorophenyl-   4-Br—C₆H₄: 4-bromophenyl-   3-Cl—C₆H₄: 3-chiorophenyl-   3-F—C₆H₄: 3-fluorophenyl-   3-Br—C₆H₄: 3-bromophenyl-   2-CH₃—C₆H₄: 2-methylphenyl-   3-CH₃—C₆H₄: 3-methylphenyl-   4-CH₃—C₆H₄: 4-methylphenyl-   2-CF₃—C₆H₄: 2-trifluoromethylphenyl-   3-CF₃—C₆H₄: 3-trifluoromethylphenyl-   4-CF₃—C₆H₄: 4-trifluoromethylphenyl-   2-CN—C₆H₄: 2-cyanophenyl-   3-CN—C₆H₄: 3-cyanophenyl-   4-CN—C₆H₄: 4-cyanophenyl-   3-CF₃—C₆H₄: 3-trifluoromethylphenyl-   4-CF₃—C₆H₄: 4-trifluoromethylphenyl-   3-NO₂—C₆H₄: 3-nitrophenyl-   2-OCH₃—C₆H₄: 2-methoxyphenyl-   3-OCH₃—C₆H₄: 3-methoxyphenyl-   4-OCH₃—C₆H₄: 4-methoxyphenyl-   3,4-Cl₂—C₆H₃: 3,4-dichlorophenyl-   3,5-Cl₂—C₆H₃: 3,5-dichlorophenyl-   2,3-Cl₂—C₆H₃: 2,3-dichlorophenyl-   2,4-Cl₂—C₆H₃: 2,4-dichlorophenyl-   2,5-Cl₂—C₆H₃: 2,5-dichlorophenyl-   2,6-Cl₂—C₆H₃: 2,6-dichlorophenyl-   3,4-F₂—C₆H₃: 3,4-difluorophenyl-   3,5-F₂—C₆H₃: 3,5-difluorophenyl-   2,3-F₂—C₆H₃: 2,3-difluorophenyl-   2,4-F₂—C₆H₃: 2,4-dichlorophenyl-   2,5-F₂—C₆H₃: 2,5-difluorophenyl-   2,6-F₂—C₆H₃: 2,6-difluorophenyl-   3-Cl-4-F—C₆H₃: 3-chloro-4-fluorophenyl-   4-Cl-3-F—C₆H₃: 4-chloro-3-fluorophenyl-   3-Br-4-F—C₆H₃: 3-bromo-4-fluorophenyl-   4-Br-3-F—C₆H₃: 4-bromo-3-fluorophenyl-   3-Br-4-Cl—C₆H₃: 3-bromo-4-chlorophenyl-   4-Br-3-Cl—C₆H₃: 4-bromo-3-chlorophenyl-   3-OH—C₆H₄: 3-hydroxyphenyl-   3,4,5-((OCH₃)₃C₆H₂): 3,4,5-trimethoxyphenyl-   3,4-(CH₃O)₂—C₆H₃: 3,4-dimethoxyphenyl-   3-CH₃O-4-F—C₆H₃: 4-fluoro-3-methoxyphenyl-   4-CH₃O-3-F—C₆H₃: 3-fluoro-4-methoxyphenyl-   2-Cl-5-NO₂—C₆H₃: 2-chloro-5-nitrophenyl-   CH₂CHCH₂: allyl-   CH₂C(CH₃)CH₂: 2-methallyl-   (CH₃)₂C═CHCH₂: 3-methylbut-2-enyl-   2-Py: 2-pyridyl-   3-Py: 3-pyridyl-   3-THF: tetrahydrofuran-3-yl-   3-THP: tetrahydropyran-3-yl-   4-THP: tetrahydropyran-4-yl-   CH₂-4-THP: tetrahydropyran-4-yl-methyl-   3-THTP: tetrahydrothiopyran-3-yl-   4-THTP: tetrahydrothiopyran-4-yl-   CH₂-4-THTP: tetrahydrothiopyran-4-yl-methyl-   4-Me-5-TZ: 4-methylthiazol-5-yl-   6,6-DM-2-N: 6,6-dimethylnorpinan-2-yl-   5,5-DM-2-TH F: 5,5-dimethyltetrahydrofuran-2-yl-   Bz: Benzyl-   1-AOE: 1-acetoxyethyl-   CH(CH₃)OCH₃: 1-methoxyethyl-   CH(CH₃)OCH(CH₃)₂: 1-isopropoxyethyl-   CH(CH₃)CH₂SCH₃: 1-methyl-2-methylsulfanylethyl-   CH₂CH₂OCH₂CH₂CH₃: 2-propoxyethyl-   CH₂CH₂OCH₂CH(CH₃)₂: 2-isobutoxyethyl-   CH(CH₃)OCH₂CH₂OCH₃: 1-(2-methoxyethoxy)ethyl-   CH(CH₃)OC₆H₅: 1-(phenoxy)ethyl-   CH(CH₃)O-c-C₆H₁₁: 1-(cyclohexyloxy)ethyl-   2-EC-c-C₃H₅: 2-ethoxycarbonylcyclopropyl-   CH(CH₃)CH(CH₃)₂: 1,2-dimethylpropyl-   4-Ip-c-C₆H₁₀: 4-isopropylcyclohexyl-   6-Ac—O—C₆H₁₂: 6-acetoxyhexyl-   CH₃—O—C(O): methoxycarbonyl-   CH₂CF₃: 2,2,2-trifluoroethyl

Compounds of formula (I) according to the present invention can beprepared e.g. according to the preparation methods and preparationschemes as described below.

Compounds of formula (I) according to the present invention can beprepared by standard methods of organic chemistry e.g. by thepreparation methods and preparation schemes as described below and inthe experimental part of this application. The definition of m, Het, X,W¹, W², W³, W⁴, R¹, R², R³, R^(4a), R^(4b) and R⁵ of the molecularstructures given in the schemes below are as defined above. Roomtemperature means a temperature range between about 20 and 25° C.

An example of a general method for the preparation of compounds offormula (I) is shown below in Scheme A. Thus, construction of theheterocyclic element 3 present in compounds of formula (I) can beachieved, for example, by alkylation of the appropriate 2-aminoheterocycle precursor 1 with the appropriate reagent of formula 2. Thetransformation is preferably carried out in polar solvents such asacetonitrile, acetone, dichloromethane, 1,4-dioxane, tetrahydrofuran,N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrolidinone or aC₁-C₆ alcohol at a temperature ranging between room temperature and thereflux temperature of the solvent. Representative reaction conditionsfor the alkylation of compounds analogous to formula 1 are given inTett. Lett. 2011, 52(23), 3033-3037. The synthesis of compounds offormula 5 can be achieved by acylation of the amine functionality incompounds of formula 3 using carboxylic acid derivatives 4 which areactivated in situ. The transformation is preferably carried out in polarsolvents such as acetonitrile, acetone, 1,4-dioxane, tetrahydrofuran,N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrolidinone or inan inert solvent such as dichloromethane, 1,2-dichloroethane, or1,2-dimethoxyethane at temperatures ranging between room temperature andthe reflux temperature of the solvent. A representative procedurecondition for the acylation is given in Journal of Medicinal Chemistry,2012, 55, 7378-7391. Examples of suitable leaving groups (LG) in formula2 include, but are not limited to: halogen, alkyl sulfonate, haloalkylsulfonate, aryl sulfonate, alkyl phosphonate. Examples of suitableleaving groups (LG²) in formula 4 include, but are not limited to:halogen, alkyl sulfonate, haloalkyl sulfonate, aryl sulfonate, alkylphosphonate and various activated esters derived from the reaction of afree carboxylic acid with a peptide coupling reagent in the presence ofan amine base (Chem. Rev., 2011, 111(11), 6557-6602). A reversal of theorder of these two steps would also result in an acceptable synthesis ofthe desired compounds.

Compounds of formula (I) can also be prepared using an alternativestrategy to install the cyano group as is shown below in Scheme B. Thus,construction of intermediate 3 proceeds as described in Scheme A, andamine functionality present in intermediates of type 3 can then beacylated with a reagent of type 6. The transformation is preferablycarried out in polar solvents such as acetonitrile, acetone,tetrahydrofuran, 1,4-dioxane, N,N-dimethylformamide,N,N-dimethylacetamide, N-methylpyrolidinone or in an inert solvent suchas dichloromethane, 1,2-dichloroethane, or 1,2-dimethoxyethane attemperatures ranging between room temperature and the reflux temperatureof the solvent. Representative procedure conditions for the acylation of3 are given in Journal of Medicinal Chemistry, 1988, 31, 4, 807-814. Inreagent 6, suitable examples of substitutent Z are: halogen, alkylsulfonate, halo alkyl sulfonate, aryl sulfonate, phosphate, phosphonate.Examples of suitable leaving groups (LG³) in formula 6 include, but arenot limited to: halogen, alkyl sulfonate or haloalkyl sulfonate, alkylphosphonate, and various activated esters derived from the reaction ofthe free carbonic acid with a peptide coupling reagent in the presenceof an amine base (Chem. Rev., 2011, 111(11), 6557-6602). In the nextstep, Z is displaced through the action of a cyanide containing compound8 to afford the desired compound 5. The transformation is preferablycarried out in polar solvents such as acetonitrile, acetone,tetrahydrofuran, 1,4-dioxane, N,N-dimethylformamide,N,N-dimethylacetamide, N-methylpyrolidinone, a C₁-C₆ alcohol or in aninert solvent such as dichloromethane, 1,2-dichloroethane,1,2-dimethoxyethane, benzene, toluene, mesitylene, cymenes, or xylenesat temperatures ranging between room temperature and the refluxtemperature of the solvent. Examples of suitable Y in formula 8 include,but are not limited to: a metal of group 1, 2, 11 or 12 of the peridodictable (by modern IUPAC numbering), hydrogen, Si(C₁-C₄-alkyl)₃ orC(CH₃)₂OH. Examples of suitable cyanide containing compounds 8 are:LiCN, NaCN, KCN, CuCN, Cu(CN)₂, Zn(CN)₂, HCN, TMS-CN(trimethylsilylcyanide), and acetone cyanohydrin. Representativeprocedure conditions for such a reaction are given in Journal ofMedicinal Chemistry, 1989, 32, 1673-1681. A reversal of the order ofthese steps would also result in an acceptable synthesis of the desiredcompounds of formula (I).

In cases where X is a sulfur atom, the sulfur atom is best installed ina subsequent step from the compound where X is an oxygen atom asdetailed in Scheme C.

Here C═O containing compound 9 is transformed into C═S containingcompound 11. The transformation is preferably carried out using areagent of substructure 10 in polar solvents such as acetonitrile,acetone, tetrahydrofuran, N,N-dimethylformamide, or in an inert solventsuch as dichloromethane, 1,2-dichloroethane, or 1,2-dimethoxyethane attemperatures ranging between room temperature and the reflux temperatureof the solvent. Suitable R^(a) groups in compounds of formula 10 are:thio, alkyl, aryl or substituted aryl. Representative reactionconditions for thionation analogous substrates are given in EuropeanJournal of Organic Chemistry, 2000, 3273-3278.

The compounds of the formula (I), and their salts are in particularsuitable for efficiently controlling arthropodal pests such asarachnids, myriapedes and insects as well as nematodes.

The compounds of the formula (I) are especially suitable for efficientlycombating insects, in particular the following pests:

Insects from the order of the lepidopterans (Lepidoptera), for exampleAcronicta major, Adoxophyes orana, Aedia leucomelas, Agrotis spp. suchas Agrotis fucosa, Agrotis segetum, Agrotis ipsilon; Alabama argillacea,Anticarsia gemmatalis, Anticarsia spp., Argyresthia conjugella,Autographa gamma, Barathra brassicae, Bucculatrix thurberiella, Bupaluspiniarius, Cacoecia murinana, Cacoecia podana, Capua reticulana,Carpocapsa pomonella, Cheimatobia brumata, Chilo spp. such as Chilosuppressalis; Choristoneura fumiferana, Choristoneura occidentalis,Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cydiapomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella,Earias insulana, Elasmopalpus lignosellus, Ephestia cautella, Ephestiakuehniella, Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp.,Evetria bouliana, Feltia spp. such as Felitia subterranean; Galleriamellonella, Grapholitha funebrana, Grapholitha molesta, Helicoverpa spp.such as Helicoverpa armigera, Helicoverpa zea; Heliothis spp. such asHeliothis armigera, Heliothis virescens, Heliothis zea; Hellula undalis,Hibernia defoliaria, Hofmannophila pseudospretella, Homona magnanima,Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Keiferialycopersicella, Lambdina fiscellaria, Laphygma spp. such as Laphygmaexigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletisblancardella, Lithophane antennata, Lobesia botrana, Loxagrotisalbicosta, Loxostege sticticalis, Lymantria spp. such as Lymantriadispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria,Mamestra spp. such as Mamestra brassicae; Mocis repanda, Mythimnaseparata, Orgyia pseudotsugata, Oria spp., Ostrinia spp. such asOstrinia nubilalis; Oulema oryzae, Panolis flammea, Pectinophora spp.such as Pectinophora gossypiella; Peridroma saucia, Phalera bucephala,Phthorimaea spp. such as Phthorimaea operculella; Phyllocnistiscitrella, Pieris spp. such as Pieris brassicae, Pieris rapae, Plathypenascabra, Putella maculipennis, Putella xyostella, Prodenia spp.,Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Rhyacioniafrustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothispilleriana, Spodoptera spp. such as Spodoptera frugiperda, Spodopteralittoralis, Spodoptera litura; Thaumatopoea pityocampa, Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia spp. such as Trichoplusia ni; Tuta absoluta, and Zeirapheracanadensis;

Beetles (Coleoptera), for example Acanthoscehdes obtectus, Adoretusspp., Agelastica alni, Agrilus sinuatus, Agriotes spp. such as Agriotesfuscicollis, Agriotes lineatus, Agriotes obscurus; Amphimallussolstitialis, Anisandrus dispar, Anobium punctatum, Anomala rufocuprea,Anoplophora spp. such as Anoplophora glabripennis; Anthonomus spp. suchas Anthonomus grandis, Anthonomus pomorum; Anthrenus spp., Aphthonaeuphoridae, Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such asAtomaria linearis; Attagenus spp., Aulacophora femoralis, Blastophaguspiniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such asBruchus lentis, Bruchus pisorum, Bruchus rufimanus; Byctiscus betulae,Callosobruchus chinensis, Cassida nebulosa, Cerotoma trifurcata, Cetoniaaurata, Ceuthorhynchus spp. such as Ceuthorrhynchus assimilis,Ceuthorrhynchus napi; Chaetocnema tibialis, Cleonus mendicus, Conoderusspp. such as Conoderus vespertinus; Cosmopolites spp., Costelytrazealandica, Crioceris asparagi, Cryptorhynchus lapath, Ctenicera spp.such as Ctenicera destructor; Curculio spp., Dectes texanus, Dermestesspp., Diabrotica spp. such as Diabrotica 12-punctata Diabroticaspeciosa, Diabrotica longicornis, Diabrotica semipunctata, Diabroticavirgifera; Epilachna spp. such as Epilachna varivestis, Epilachnavigintioctomaculata; Epitrix spp. such as Epitrix hirtipennis,Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides,Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupesbajulus, Hypera brunneipennis, Hypera postica, Hypothenemus spp., Ipstypographus, Lachnosterna consanguinea, Lema bilineata, Lema melanopus,Leptinotarsa spp. such as Leptinotarsa decemlineata; Limoniuscalifornicus, Lissorhoptrus oryzophilus, Lissorhoptrus oryzophilus,Lixus spp., Lyctus spp. such as Lyctus bruneus; Melanotus communis,Meligethes spp. such as Meligethes aeneus; Melolontha hippocastani,Melolontha melolontha, Migdolus spp., Monochamus spp. such as Monochamusalternatus; Naupactus xanthographus, Niptus hololeucus, Oryctesrhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus,Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema oryzae, Oxycetoniajucunda, Phaedon cochleariae, Phyllobius pyri, Phyllopertha horticola,Phyllophaga spp., Phyllotreta spp. such as Phyllotreta chrysocephala,Phyllotreta nemorum, Phyllotreta striolata; Phyllophaga spp.,Phyllopertha horticola, Popillia japonica, Premnotrypes spp., Psylliodeschrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica,Sitona lineatus, Sitophilus spp. such as Sitophilus granaria, Sitophiluszeamais; Sphenophorus spp. such as Sphenophorus levis; Sternechus spp.such as Sternechus subsignatus; Symphyletes spp., Tenebrio molitor,Tribolium spp. such as Tribolium castaneum; Trogoderma spp., Tychiusspp., Xylotrechus spp., and Zabrus spp. such as Zabrus tenebrioides;

Flies, mosquitoes (Diptera), e.g. Aedes spp. such as Aedes aegypti,Aedes albopictus, Aedes vexans; Anastrepha ludens, Anopheles spp. suchas Anopheles albimanus, Anopheles crucians, Anopheles freeborni,Anopheles gambiae, Anopheles leucosphyrus, Anopheles maculipennis,Anopheles minimus, Anopheles quadrimaculatus, Anopheles sinensis; Bibiohortulanus, Calliphora erythrocephala, Calliphora vicina, Cerafitiscapitata, Ceratitis capitata, Chrysomyia spp. such as Chrysomyabezziana, Chrysomya hominivorax, Chrysomya macellaria; Chrysopsatlanticus, Chrysops discalis, Chrysops silacea, Cochliomyia spp. suchas Cochliomyla hominivorax; Contarinia spp. such as Contariniasorghicola; Cordylobia anthropophaga, Culex spp. such as Culexnigripalpus, Culex pipens, Culex quinquefasciatus, Culex tarsalis, Culextritaeniorhynchus; Culicoides furens, Culiseta inornata, Culisetamelanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineurabrassicae, Delia spp. such as Delia antique, Delia coarctata, Deliaplatura, Delia radicum; Dermatobia hominis, Drosophila spp., Fannia spp.such as Fannia canicularis; Gastraphilus spp. such as Gasterophilusintestinalis; Geomyza Tripunctata, Glossina fuscipes, Glossinamorsitans, Glossina palpalis, Glossina tachinoides, Haematobia irritans,Haplodiplosis equestris, Hippelates spp., Hylemyia spp. such as Hylemyiaplatura; Hypoderma spp. such as Hypoderma lineata; Hyppobosca spp.,Leptoconops torrens, Liriomyza spp. such as Liriomyza sativae, Liriomyzatrifolii; Lucilia spp. such as Lucilia caprina, Lucilia cuprina, Luciliasericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. suchas Mayetiola destructor; Musca spp. such as Musca autumnalis, Muscadomestica; Muscina stabulans, Oestrus spp. such as Oestrus ovis; Opomyzaflorum, Oscinella spp. such as Oscinella frit; Pegomya hysocyam,Phlebotomus argentipes, Phorbia spp. such as Phorbia antiqua, Phorbiabrassicae, Phorbia coarctata; Prosimulium mixtum, Psila rosae,Psorophora columbiae, Psorophora discolor, Rhagoletis ceras, Rhagoletispomonella, Sarcophaga spp. such as Sarcophaga haemorrhoidalis; Simuliumvittatum, Stomoxys spp. such as Stomoxys calcitrans; Tabanus spp. suchas Tabanus atratus, Tabanus bovinus, Tabanus lineola, Tabanus similis;Tannia spp., Tipula oleracea, Tipula paludosa, and Wohlfahrtia spp.;

Thrips (Thysanoptera), e.g. Baliothrips biformis, Dichromothripscorbetti, Dichromothrips ssp., Enneothrips flavens, Frankliniella spp.such as Frankiniella fusca, Frankiniella occidentalis, Frankiniellatritici; Heliothrips spp., Hercinothrips femoralis, Kakothrips spp.,Rhipiphorothrips cruentatus, Scirtothrips spp. such as Scirtothripscitri; Taeniothrips cardamon, Thrips spp. such as Thrips oryzae, Thripspalmi, Thrips tabaci;

Termites (Isoptera), e.g. Calotermes flavicollis, Coptotermesformosanus, Heterotermes aureus, Heterotermes longiceps, Heterotermestenuis, Leucotermes flavipes, Odontotermes spp., Reticulitermes spp.such as Reticulitermes speratus, Reticulitermes flavipes, Reticulitermesgrassei, Reticulitermes lucifugus, Reticulitermes santonensis,Reticulitermes virginicus; Termes natalensis;

Cockroaches (Blattaria-Blattodea), e.g. Acheta domesticus, Blattaorientalis, Battella asahinae, Blattella germanica, Gryllotalpa spp.,Leucophaea maderae, Locusta spp., Melanoplus spp., Periplanetaamericana, Periplaneta australasiae, Periplaneta brunnea, Periplanetafuligginosa, Periplaneta japonica;

Bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas(Hemiptera), e.g. Acrosternum spp. such as Acrosternum hilare;Acyrthosipon spp. such as Acyrthosiphon onobrychis, Acyrthosiphon pisum,Adelges laricis, Aeneolamia spp., Agonoscena spp., Aleurodes spp.,Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis,Antestiopsis spp., Anuraphis cardu, Aonidiella spp., Aphanostigma pirAphidula nasturtii, Aphis spp. such as Aphis fabae, Aphis forbesi, Aphisgossypi, Aphis grossulariae, Aphis pomi, Aphis sambuci Aphis schneider,Aphis spiraecola; Arboridia apicalis, Arilus critatus, Aspidiella spp.,Aspidiotus spp., Atanus spp., Aulacorthum solanm Bemisia spp. such asBemisia argentifolii, Bemisia tabaci; Blissus spp. such as Blissusleucopterus; Brachycaudus cardu, Brachycaudus helichrys, Brachycauduspersicae, Brachycaudus prunicola, Brachycolus spp., Brevicorynebrassicae, Calligypona marginata, Calocoris spp., Campylomma livida,Capitophorus horni, Carneocephala fulgida, Cavelerius spp., Ceraplastesspp., Ceratovacuna lanigera, Cercopidae, Cerosipha gossypii,Chaetosiphon fragaefoli, Chionaspis tegalensis, Chlorita onukii,Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Cimexspp. such as Cimexhemipterus, Cimex lectularius; Coccomytilus hali,Coccus spp., Creontiades dilutus, Cryptomyzus ribis, Cryptomyzus ribis,Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeurades spp.,Diaphorina spp., Diaspis spp., Dichelops furcatus, Diconocoris hewett,Doralis spp., Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha spp.,Dysaphis spp. such as Dysaphis plantaginea, Dysaphis pyri, Dysaphisradicola; Dysaulacorthum pseudosoani, Dysdercus spp. such as Dysdercuscingulatus, Dysdercus intermedius; Dysmicoccus spp., Empoasca spp. suchas Empoasca fabae, Empoasca solana; Eriosoma spp., Erythroneura spp.,Eurygaster spp. such as Eurygaster integriceps; Euscelis bilobatus,Euschistus spp. such as Euschistuos heros, Euschistus impictiventris,Euschistus servus; Geococcus coffeae, Halyomorpha spp. such asHalyomorpha halys; Heliopeltis spp., Homalodisca coagulata, Horciasnobilellus, Hyalopterus pruni, Hyperomyzus lactucae, Icerya spp.,Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp.,Lepidosaphes spp., Leptocorisa spp., Leptoglossus phyllopus, Lipaphiserysimi, Lygus spp. such as Lygus hesperus, Lygus lineolaris, Lyguspratensis; Macropes excavatus, Macrosiphum spp. such as Macrosiphumrosae, Macrosiphum avenae, Macrosiphum euphorbiae, Mahanarvafimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius,Melanaphis sacchar, Metcafiella spp., Metopolophium dirhodum, Miridaespp., Monellia costalis, Monelliopsis pecanis, Myzus spp. such as Myzusascalonicus, Myzus cerasi, Myzus persicae, Myzus varians; Nasonoviaribis-nigr, Nephotettix spp. such as Nephotettixmalayanus,Nephotettixnigropictus, Nephotettixparvus, Nephotettix virescens; Nezaraspp. such as Nezara viridula; Nilaparvata lugens, Oebalus spp.,Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratriozaspp., Parlatoria spp., Pemphigus spp. such as Pemphigus bursarius;Pentomidae, Peregrinus maidis, Perkinsiella saccharicida, Phenacoccusspp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Piesmaquadrata, Piezodorus spp. such as Piezodorus guildinii, Pinnaspisaspidistrae, Planococcus spp., Protopulvinaria pyriformis, Psallusseriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcusspp. such as Pseudococcus comstocki; Psylla spp. such as Psylla mali,Psylla piri; Pteromalus spp., Pyrilla spp., Quadraspidiotus spp.,Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhodnius spp.,Rhopalomyzus ascalonicus, Rhopalosiphum spp. such as Rhopalosiphumpseudobrassicas, Rhopalosiphum insertum, Rhopalosiphum maidis,Rhopalosiphum padi; Sagatodes spp., Sahlbergella singularis, Saissetiaspp., Sappaphis mala, Sappaphis mali, Scaphoides titanus, Schizaphisgraminum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidusarticulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solubeainsularis, Stephanitis nashi, Stictocephala festina, Tenalapharamalayensis, Thyanta spp. such as Thyanta perditor; Tibraca spp.,Tinocalis caryaefoliae, Tomaspis spp., Toxoptera spp. such as Toxopteraaurantii; Trialeurodes spp. such as Trialeurodes vaporariorum; Triatomaspp., Trioza spp., Typhlocyba spp., Unaspis spp. such as Unaspisyanonensis; and Viteus vitifolii;

Ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Attacapiguara, Atta cephalotes, Atta cephalotes, Atta laevigata, Attarobusta, Atta sexdens, Atta texana, Bombus spp., Camponotus floridanus,Crematogaster spp., Dasymutilla occidentalis, Diprion spp.,Dolichovespula maculata, Hoplocampa spp. such as Hoplocampa minuta,Hoplocampa testudinea; Lasius spp. such as Lasius niger, Linepithemahumile, Monomorium pharaonis, Paravespula germanica, Paravespulapennsylvanica, Paravespula vulgaris, Pheidole megacephala, Pogonomyrmexbarbatus, Pogonomyrmex californicus, Polistes rubiginosa, Solenopsisgeminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni,Vespa spp. such as Vespa crabro, and Vespula squamosal;

Crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica,Calliptamus italicus, Chortoicetes terminifera, Dociostaurus maroccanus,Gryllotalpa africana, Gryllotalpa gryllotalpa, Hieroglyphus daganensis,Kraussaria angulifera, Locusta migratoria, Locustana pardalina,Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus,Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata,Oedaleus senegalensis, Schistocerca americana, Schistocerca gregaria,Tachycines asynamorus, and Zonozerus variegatus;

Earwigs (Dermaptera), e.g. forficula auricularia,

Lice (Phthiraptera), e.g. Damalinia spp., Pediculus spp. such asPediculus humanus capitis, Pediculus humanus corporis; Pthirus pubis,Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis,Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopongallinae, Menacanthus stramineus and Solenopotes capillatus,Trichodectes spp.;

Fleas (Siphonaptera), e.g. Ceratophyllus spp., Ctenocephaldes felis,Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tungapenetrans, and Nosopsyllus fasciatus.

The compounds of the formula (I) are also suitable for efficientlycombating arthropd pests different from insects such as, in particularthe following pests:

arachnids (Arachnida), such as acari, e.g. of the families Argasidae,Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. Amblyommaamericanum, Amblyomma variegatum, Amblyomma maculatum), Argas spp. (e.g.Argas persicus), Boophilus spp. (e.g. Boophilus annulatus, Boophilusdecoloratus, Boophilus microplus), Dermacentor silvarum, Dermacentorandersoni, Dermacentor variabilis, Hyalomma spp. (e.g. Hyalommatruncatum), Ixodes spp. (e.g. Ixodes ricinus, Ixodes rubicundus, Ixodesscapularis, Ixodes holocyclus, Ixodes pacificus), Ornithodorus spp.(e.g. Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata),Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptesspp. (e.g. Psoroptes ovis), Rhipicephalus spp. (e.g. Rhipicephalussanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi),Rhizoglyphus spp., Sarcoptes spp. (e.g. Sarcoptes scabiel), andEriophyidae spp. such as Acaria sheldoni Aculops spp. (e.g. Aculopspelekassi) Aculus spp. (e.g. Aculus schlechtendali), Epitrimerus pyri,Phyllocoptruta oleivora and Eriophyes spp. (e.g. Eriophyes sheldoni);Tarsonemidae spp. such as Hemitarsonemus spp., Phytonemus pallidus andPolyphagotarsonemus latus, Stenotarsonemus spp.; Tenuipalpidae spp. suchas Brevipalpus spp. (e.g. Brevipalpus phoenicis); Tetranychidae spp.such as Eotetranychus spp., Eutetranychus spp., Oligonychus spp.,Tetranychus cinnabarinus, Tetranychus kanzawa, Tetranychus pacificus,Tetranychus telarius and Tetranychus urticae; Bryobia praetiosa,Panonychus spp. (e.g. Panonychus ulmi Panonychus citri), Metatetranychusspp. and Oligonychus spp. (e.g. Oligonychus pratensis), Vasateslycopersici; Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa.And Acarus siro, Chorioptes spp., Scorpio maurus;

Silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobiadomestica;

Centipedes (Chilopoda), e.g. Geophilus spp., Scutigera spp. such asScutigera coleoptrata;

Millipedes (Diplopoda), e.g. Blaniulus guttulatus, Narceus spp.,

Springtails (Collembola), e.g. Onychiurus ssp. such as Onychiurusarmatus,

They are also suitable for controlling nematodes: plant parasiticnematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyneincognita, Meloidogyne javanica, and other Meloidogyne species;cyst-forming nematodes, Globodera rostochiensis and other Globoderaspecies; Heterodera avenae, Heterodera glycines, Heterodera schachtii,Heterodera trifolli, and other Heterodera species; Seed gall nematodes,Anguina species; Stem and foliar nematodes, Aphelenchoides species suchas Aphelenchoides besseyi; Sting nematodes, Belonolaimus longicaudatusand other Belonolaimus species; Pine nematodes, Bursaphelenchuslignicolus Mamiya et Kiyohara, Bursaphelenchus xylophilus and otherBursaphelenchus species; Ring nematodes, Criconema species, Criconemellaspecies, Criconemoides species, Mesocriconema species; Stem and bulbnematodes, Ditylenchus destructor, Ditylenchus dipsaci and otherDitylenchus species; Awl nematodes, Dolichodorus species; Spiralnematodes, Heliocotylenchus multicinctus and other Helicotylenchusspecies; Sheath and sheathoid nematodes, Hemicycliophora species andHemicriconemoides species; Hirshmanniella species; Lance nematodes,Hoploaimus species; false rootknot nematodes, Nacobbus species; Needlenematodes, Longidorus elongatus and other Longidorus species; Lesionnematodes, Pratylenchus brachyurus, Pratylenchus neglectus, Pratylenchuspenetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and otherPratylenchus species; Burrowing nematodes, Radopholus similis and otherRadopholus species; Reniform nematodes, Rotylenchus robustus,Rotylenchus reniformis and other Rotylenchus species; Scutellonemaspecies; Stubby root nematodes, Trichodorus primitivus and otherTrichodorus species, Paratrichodorus species; Stunt nematodes,Tylenchorhynchus claytoni Tylenchorhynchus dubius and otherTylenchorhynchus species; Citrus nematodes, Tylenchulus species such asTylenchulus semipenetrans, Dagger nematodes, Xiphinema species; andother plant parasitic nematode species.

Examples of further pest species which may be controlled by compounds offormula (I) include: from the class of the Bivalva, for example,Dreissena spp.; from the class of the Gastropoda, for example, Arionspp., Biomphalaria spp., Buliinus spp., Deroceras spp., Galba spp.,Lymnaea spp., Oncomelania spp., Succinea spp.; from the class of thehelminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum,Acylostoma brazilensis, Ancylostoma spp., Ascaris lubricoides, Ascarisspp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp.,Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria,Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus,Echinococcus multilocularis, Enterobius vermicularis, Faciola spp.,Haemonchus spp. such as Haemonchus contortus; Heterakis spp.,Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp.,Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagiaspp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni,Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taeniasolium, Trichinella spiralis, Trichinella nativa, Trichinella britovi,Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp.,Trichuris trichiura, Wuchereria bancrofti; from the order of theIsopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellioscaber; from the order of the Symphyla, for example, Scutigerellaimmaculata.

Further examples of pest species which may be controlled by compounds offormula (I) include: Anisoplia austriaca, Apamea spp., Austroascaviridigrisea, Baliothrips biformis, Caenorhabditis elegans, Cephus spp.,Ceutorhynchus napi, Chaetocnema aridula, Chilo auricilius, Chiloindicus, Chilo polychrysus, Chortiocetes terminifera, Cnaphalocrocimedinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp.,Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulusmaidis, Deraceras reticulatum, Diatrea saccharalis, Dichelops furcatus,Dicladispa armigera, Diloboderus spp. such as Diloboderus abderus;Edessa spp., Epinotia spp., Formicidae, Geocoris spp., Globitermessulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor,Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta,Leptocorsia oratorius, Liogenys fuscus, Lucillia spp., Lyogenys fuscus,Mahanarva spp., Maladera matrida, Marasmia spp., Mastotermes spp.,Mealybugs, Megascelis ssp, Metamasius hemipterus, Microtheca spp., Mocislatipes, Murgantia spp., Mythemina separata, Neocapritermes opacus,Neocapritermes parvus, Neomegalotomus spp., Neotermes spp., Nymphuladepunctalis, Oebalus pugnax, Orseolia spp. such as Orseolia oryzae,Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata,Procornitermes ssp, Procornitermes triacifer, Psylloides spp.,Rachiplusia spp., Rhodopholus spp., Scaptocoris castanea, Scaptocorisspp., Scirpophaga spp. such as Scirpophaga incertulas, Scirpophagainnotata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp.such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata,Spissistilus spp., Stalk borer, Stenchaetothrips biformis,Steneotarsonemus spinki, Sylepta derogata, Telehin licus,Trichostrongylus spp.

Compounds of the formula (I) are particularly useful for controllinginsects of the orders Hemiptera and Thysanoptera.

For use in a method according to the present invention, the compounds ofthe formula (I) can be converted into the customary formulations, e.g.solutions, emulsions, suspensions, dusts, powders, pastes, granules anddirectly sprayable solutions. The use form depends on the particularpurpose and application method. Formulations and application methods arechosen to ensure in each case a fine and uniform distribution of thecompound of the formula (I) according to the present invention.

The formulations are prepared in a known manner (see e.g. for reviewU.S. Pat. No. 3,060,084, EP-A 707 445 (for liquid concentrates),Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48,Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York,1963, pages 8-57 and et seq. WO 91/13546, U.S. Pat. No. 4,172,714, U.S.Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, U.S. Pat. No. 5,180,587,U.S. Pat. No. 5,232,701, U.S. Pat. No. 5,208,030, GB 2,095,558, U.S.Pat. No. 3,299,566, Klingman, Weed Control as a Science, John Wiley andSons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H.,Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim(Germany), 2001, 2. D. A. Knowles, Chemistry and Technology ofAgrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998(ISBN 0-7514-0443-8), for example by extending the active compound withauxiliaries suitable for the formulation of agrochemicals, such assolvents and/or carriers, if desired emulsifiers, surfactants anddispersants, preservatives, antifoaming agents, anti-freezing agents,for seed treatment formulation also optionally colorants and/or bindersand/or gelling agents.

Solvents/carriers, which are suitable, are e.g.:

-   -   solvents such as water, aromatic solvents (for example Solvesso        products, xylene and the like), paraffins (for example mineral        fractions), alcohols (for example methanol, butanol, pentanol,        benzyl alcohol), ketones (for example cyclohexanone,        gamma-butyrolactone), pyrrolidones (N-methyl-pyrrolidone (NMP),        N-octylpyrrolidone NOP), acetates (glycol diacetate), alkyl        lactates, lactones such as g-butyrolactone, glycols, fatty acid        dimethylamides, fatty acids and fatty acid esters,        triglycerides, oils of vegetable or animal origin and modified        oils such as alkylated plant oils. In principle, solvent        mixtures may also be used.    -   carriers such as ground natural minerals and ground synthetic        minerals, such as silica gels, finely divided silicic acid,        silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole,        loess, clay, dolomite, diatomaceous earth, calcium sulfate and        magnesium sulfate, magnesium oxide, ground synthetic materials,        fertilizers, such as, for example, ammonium sulfate, ammonium        phosphate, ammonium nitrate, ureas and products of vegetable        origin, such as cereal meal, tree bark meal, wood meal and        nutshell meal, cellulose powders and other solid carriers.

Suitable emulsifiers are nonionic and anionic emulsifiers, for examplepolyoxyethylene fatty alcohol ethers, alkylsulfonates andarylsulfonates.

Examples of dispersants are lignin-sulfite waste liquors andmethylcellulose.

Suitable surfactants are alkali metal, alkaline earth metal and ammoniumsalts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonicacid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids andsulfated fatty alcohol glycol ethers, furthermore condensates ofsulfonated naphthalene and naphthalene derivatives with formaldehyde,condensates of naphthalene or of naphthalenesulfonic acid with phenoland formaldehyde, polyoxyethylene octylphenyl ether, ethoxylatedisooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers,tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether,alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxidecondensates, ethoxylated castor oil, polyoxyethylene alkyl ethers,ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal,sorbitol esters,

Also anti-freezing agents such as glycerin, ethylene glycol, propyleneglycol and bactericides such as can be added to the formulation.

Suitable antifoaming agents are for example antifoaming agents based onsilicon or magnesium stearate.

Suitable preservatives are for example dichlorophen und benzyl alcoholhemiformal

Suitable thickeners are compounds which confer a pseudoplastic flowbehavior to the formulation, i.e. high viscosity at rest and lowviscosity in the agitated stage. Mention may be made, in this context,for example, of commercial thickeners based on polysaccharides, such asXanthan Gum® (Kelzan® from Kelco), Rhodopol®23 (Rhone Poulenc) orVeegum® (from R.T. Vanderbilt), or organic phyllosilicates, such asAttaclay® (from Engelhardt). Antifoam agents suitable for thedispersions according to the invention are, for example, siliconeemulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® fromRhodia), long-chain alcohols, fatty acids, organofluorine compounds andmixtures thereof. Biocides can be added to stabilize the compositionsaccording to the invention against attack by microorganisms. Suitablebiocides are, for example, based on isothiazolones such as the compoundsmarketed under the trademarks Proxel® from Avecia (or Arch) or Acticide®RS from Thor Chemie and Kathon® MK from Rohm & Haas. Suitable antifreezeagents are organic polyols, for example ethylene glycol, propyleneglycol or glycerol. These are usually employed in amounts of not morethan 10% by weight, based on the total weight of the active compoundcomposition. If appropriate, the active compound compositions accordingto the invention may comprise 1 to 5% by weight of buffer, based on thetotal amount of the formulation prepared, to regulate the pH, the amountand type of the buffer used depending on the chemical properties of theactive compound or the active compounds. Examples of buffers are alkalimetal salts of weak inorganic or organic acids, such as, for example,phosphoric acid, boronic acid, acetic acid, propionic acid, citric acid,fumaric acid, tartaric acid, oxalic acid and succinic acid.

Substances which are suitable for the preparation of directly sprayablesolutions, emulsions, pastes or oil dispersions are mineral oilfractions of medium to high boiling point, such as kerosene or dieseloil, furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, for example toluene,xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or theirderivatives, methanol, ethanol, propanol, butanol, cyclohexanol,cyclohexanone, isophorone, strongly polar solvents, for example dimethylsulfoxide, N-methylpyrrolidone and water.

Powders, materials for spreading and dusts can be prepared by mixing orconcomitantly grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active ingredientsto solid carriers. Examples of solid carriers are mineral earths such assilica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk,bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate,magnesium sulfate, magnesium oxide, ground synthetic materials,fertilizers, such as, for example, ammonium sulfate, ammonium phosphate,ammonium nitrate, ureas, and products of vegetable origin, such ascereal meal, tree bark meal, wood meal and nutshell meal, cellulosepowders and other solid carriers.

In general, the formulations comprise from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the active ingredient. Theactive ingredients are employed in a purity of from 90% to 100%,preferably 95% to 100% (according to NMR spectrum).

For seed treatment purposes, respective formulations can be diluted 2-10fold leading to concentrations in the ready to use preparations of 0.01to 60% by weight active compound by weight, preferably 0.1 to 40% byweight.

The compound of formula (I) can be used as such, in the form of theirformulations or the use forms prepared therefrom, for example in theform of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dustable products,materials for spreading, or granules, by means of spraying, atomizing,dusting, spreading or pouring. The use forms depend entirely on theintended purposes; they are intended to ensure in each case the finestpossible distribution of the active compounds according to theinvention.

The following are examples of formulations:

-   1. Products for dilution with water. For seed treatment purposes,    such products may be applied to the seed diluted or undiluted.

A) Water-Soluble Concentrates (SL, LS)

10 parts by weight of the active compound is dissolved in 90 parts byweight of water or a water-soluble solvent. As an alternative, wettersor other auxiliaries are added. The active compound dissolves upondilution with water, whereby a formulation with 10% (w/w) of activecompound is obtained.

B) Dispersible Concentrates (DC)

20 parts by weight of the active compound is dissolved in 70 parts byweight of cyclohexanone with addition of 10 parts by weight of adispersant, for example polyvinylpyrrolidone. Dilution with water givesa dispersion, whereby a formulation with 20% (w/w) of active compoundsis obtained.

C) Emulsifiable Concentrates (EC)

15 parts by weight of the active compounds is dissolved in 7 parts byweight of xylene with addition of calcium dodecylbenzenesulfonate andcastor oil ethoxylate (in each case 5 parts by weight). Dilution withwater gives an emulsion, whereby a formulation with 15% (w/w) of activecompounds is obtained.

D) Emulsions (EW, EO, ES)

25 parts by weight of the active compound is dissolved in 35 parts byweight of xylene with addition of calcium dodecylbenzenesulfonate andcastor oil ethoxylate (in each case 5 parts by weight). This mixture isintroduced into 30 parts by weight of water by means of an emulsifiermachine (e.g. Ultraturrax) and made into a homogeneous emulsion.Dilution with water gives an emulsion, whereby a formulation with 25%(w/w) of active compound is obtained.

E) Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of the active compound iscomminuted with addition of 10 parts by weight of dispersants, wettersand 70 parts by weight of water or of an organic solvent to give a fineactive compound suspension. Dilution with water gives a stablesuspension of the active compound, whereby a formulation with 20% (w/w)of active compound is obtained.

F) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50 parts by weight of the active compound is ground finely with additionof 50 parts by weight of dispersants and wetters and made aswater-dispersible or water-soluble granules by means of technicalappliances (for example extrusion, spray tower, fluidized bed). Dilutionwith water gives a stable dispersion or solution of the active compound,whereby a formulation with 50% (w/w) of active compound is obtained.

G) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, SS, WS)

75 parts by weight of the active compound are ground in a rotor-statormill with addition of 25 parts by weight of dispersants, wetters andsilica gel. Dilution with water gives a stable dispersion or solution ofthe active compound, whereby a formulation with 75% (w/w) of activecompound is obtained.

H) Gel-Formulation (GF)

In an agitated ball mill, 20 parts by weight of the active compound iscomminuted with addition of 10 parts by weight of dispersants, 1 part byweight of a gelling agent wetters and 70 parts by weight of water or ofan organic solvent to give a fine active compound suspension. Dilutionwith water gives a stable suspension of the active compound, whereby aformulation with 20% (w/w) of active compound is obtained.

-   2. Products to be applied undiluted for foliar applications. For    seed treatment purposes, such products may be applied to the seed    diluted or undiluted.

I) Dustable Powders (DP, DS)

5 parts by weight of the active compound are ground finely and mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dustable product having 5% (w/w) of active compound.

J) Granules (GR, FG, GG, MG)

0.5 part by weight of the active compound is ground finely andassociated with 95.5 parts by weight of carriers, whereby a formulationwith 0.5% (w/w) of active compound is obtained. Current methods areextrusion, spray-drying or the fluidized bed. This gives granules to beapplied undiluted for foliar use.

K) ULV Solutions (UL)

10 parts by weight of the active compound is dissolved in 90 parts byweight of an organic solvent, for example xylene. This gives a producthaving 10% (w/w) of active compound, which is applied undiluted forfoliar use.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwettable powders (sprayable powders, oil dispersions) by adding water.To prepare emulsions, pastes or oil dispersions, the substances, as suchor dissolved in an oil or solvent, can be homogenized in water by meansof a wetter, tackifier, dispersant or emulsifier. Alternatively, it ispossible to prepare concentrates composed of active substance, wetter,tackifier, dispersant or emulsifier and, if appropriate, solvent or oil,and such concentrates are suitable for dilution with water.

The active ingredient concentrations in the ready-to-use products can bevaried within relatively wide ranges. In general, they are from 0.0001to 10%, preferably from 0.01 to 1%.

The active ingredients may also be used successfully in theultra-low-volume process (ULV), it being possible to apply formulationscomprising over 95% by weight of active ingredient, or even to apply theactive ingredient without additives.

In the method of this invention compounds of formula (I) may be appliedwith other active ingredients, for example with other pesticides,insecticides, herbicides, fertilizers such as ammonium nitrate, urea,potash, and superphosphate, phytotoxicants and plant growth regulators,safeners and nematicides. These additional ingredients may be usedsequentially or in combination with the above-described compositions, ifappropriate also added only immediately prior to use (tank mix). Forexample, the plant(s) may be sprayed with a composition of thisinvention either before or after being treated with other activeingredients.

M.1 Acetylcholine esterase (AChE) inhibitors from the class of

M.1A carbamates, for example aldicarb, alanycarb, bendiocarb,benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran,carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb,isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb andtriazamate; or from the class of

M.1B organophosphates, for example acephate, azamethiphos,azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos,chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl,coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate,heptenophos, imicyafos, isofenphos, isopropylO-(methoxy-aminothio-phosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate,phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl,profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion,quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;

M.2. GABA-gated chloride channel antagonists such as:

M.2A cyclodiene organochlorine compounds, as for example endosulfan orchlordane; or

M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil,flufiprole, pyrafluprole and pyriprole;

M.3 Sodium channel modulators from the class of

M.3A pyrethroids, for example acrinathrin, allethrin, d-cis-transallethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrinS-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin,esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate,flumethrin, tau-fluvalinate, halfenprox, imiprothrin, meperfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin,profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin,tetramethylfluthrin, tetramethrin, tralomethrin and transfluthrin; or

M.3B sodium channel modulators such as DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class of

M.4A neonicotinoids, for example acteamiprid, chlothianidin,dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; orthe compounds

M.4A.1:1-[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-(5S,8R)-5,8-Epoxy-1H-imidazo[1,2-a]azepine; or

M.4A.2:1-[(6-chloro-3-pyridyl)methyl]-2-nitro-1-[(E)-pentylideneamino]guanidine;or

M4.A.3:1-[(6-chloro-3-pyridyl)methyl]-7-methyl-8-nitro-5-propoxy-3,5,6,7-tetrahydro-2H-imidazo[1,2-a]pyridine;

or M.4B nicotine.

M.5 Nicotinic acetylcholine receptor allosteric activators from theclass of spinosyns, for example spinosad or spinetoram;

M.6 Chloride channel activators from the class of avermectins andmilbemycins, for example abamectin, emamectin benzoate, ivermectin,lepimectin or milbemectin;

M.7 Juvenile hormone mimics, such as

M.7A juvenile hormone analogues as hydroprene, kinoprene and methoprene;or others as M.7B fenoxycarb or M.7C pyriproxyfen;

M.8 miscellaneous non-specific (multi-site) inhibitors, for example

M.8A alkyl halides as methyl bromide and other alkyl halides, or

M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8Etartar emetic;

M.9 Selective homopteran feeding blockers, for example

M.9B pymetrozine, or M.9C flonicamid;

M.10 Mite growth inhibitors, for example

M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;

M.11 Microbial disruptors of insect midgut membranes, for examplebacillus thuringiensis or bacillus sphaericus and the insecticdalproteins they produce such as bacillus thuringiensis subsp. israelensis,bacillus sphaericus, bacillus thuringiensis subsp. aizawai bacillusthuringiensis subsp. kurstaki and bacillus thuringiensis subsp.tenebrionis, or the Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab,mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1;

M.12 Inhibitors of mitochondrial ATP synthase, for example

M.12A diafenthiuron, or

M.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatinoxide, or M.12C propargite, or M.12D tetradifon;

M.13 Uncouplers of oxidative phosphorylation via disruption of theproton gradient, for example chlorfenapyr, DNOC or sulfluramid;

M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, forexample nereistoxin analogues as bensultap, cartap hydrochloride,thiocyclam or thiosultap sodium;

M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureasas for example bis-trifluron, chlorfluazuron, diflubenzuron,flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron, teflubenzuron or triflumuron;

M.16 Inhibitors of the chitin biosynthesis type 1, as for examplebuprofezin;

M.17 Moulting disruptors, Dipteran, as for example cyromazine;

M.18 Ecdyson receptor agonists such as diacylhydrazines, for examplemethoxyfenozide, tebufenozide, halofenozide, fufenozide orchromafenozide;

M.19 Octopamin receptor agonists, as for example amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, forexample

M.20A hydramethylnon, or M.20B acequinocyl, or M.20C fluacrypyrim;

M.21 Mitochondrial complex I electron transport inhibitors, for example

M.21A METI acaricides and insecticides such as fenazaquin,fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, orM.21B rotenone;

M.22 Voltage-dependent sodium channel blockers, for example

M.22A indoxacarb, or M.22B metaflumizone, or M.22C1-[(E)-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]amino]-3-[4-(difluoromethoxy)phenyl]urea;

M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic andTetramic acid derivatives, for example spirodiclofen, spiromesifen orspirotetramat;

M.24 Mitochondrial complex IV electron transport inhibitors, for example

M.24A phosphine such as aluminium phosphide, calcium phosphide,phosphine or zinc phosphide, or M.24B cyanide.

M.25 Mitochondrial complex II electron transport inhibitors, such asbeta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;

M.28 Ryanodine receptor-modulators from the class of diamides, as forexample flubendiamide, chlorantraniliprole (Rynaxypyr®),cyantraniliprole (Cyazypyr®), or the phthalamide compounds

M.28.1:(R)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamidand

M.28.2:(S)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,or the compound

M.28.3:3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chlorpyridin-2-yl)-1H-pyrazole-5-carboxamide(proposed ISO name: cyclaniliprole), or the compound

M.28.4:methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate;or a compound selected from M.28.5a) to M.28.5l):

M.28.5a)N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5b)N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5c)N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5d)N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5e)N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide;

M.28.5f)N-[4,6-dibromo-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5g)N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5h)N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5i)N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methyl-phenyl]-5-bromo-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide;

M.28.5j)5-chloro-2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(1-cyano-1-methyl-ethyl)carbamoyl]phenyl]pyrazole-3-carboxamide;

M.28.5k)5-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-2-(3,5-dichloro-2-pyridyl)pyrazole-3-carboxamide;

M.28.5l)N-[2-(tert-butylcarbamoyl)-4-chloro-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(fluoromethoxy)pyrazole-3-carboxamide;or a compound selected from

M.28.6N2-(1-cyano-1-methyl-ethyl)-N1-(2,4-dimethylphenyl)-3-iodo-phthalamide;or

M.28.73-chloro-N2-(1-cyano-1-methyl-ethyl)-N1-(2,4-dimethylphenyl)phthalamide;

M.UN.X insecticidal active compounds of unknown or uncertain mode ofaction, as for example afidopyropen, azadirachtin, amidoflumet,benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite,dicofol, flufenerim, flometoquin, fluensulfone, flupyradifurone,piperonyl butoxide, pyridalyl, pyrifluquinazon, sulfoxaflor, pyflubumideor the compounds

M.UN.X.1:4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide,or the compound

M.UN.X.2:4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1-carboxamide,or the compound

M.UN.X.3:11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one,or the compound

M.UN.X.4:3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,or the compound

M.UN.X.5:1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine,or actives on basis of bacillus firmus (Votivo, 1-1582); or

M.UN.X.6; a compound selected from the group of

M.UN.X.6a)(E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamide;

M.UN.X.6b)(E/Z)—N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamide;

M.UN.X.6c)(E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide

M.UN.X.6d)(E/Z)—N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamide;

M.UN.X.6e)(E/Z)—N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoroacetamide;

M.UN.X.6f)(E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;

M.UN.X.6g)(E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;

M.UN.X.6h)(E/Z)—N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamideand

M.UN.X.6i)(E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoropropanamide);or of the compounds

M.UN.X.7:3-[3-chloro-5-(trifluoromethyl)phenyl]-4-oxo-1-(pyrimidin-5-ylmethyl)pyrido[1,2-a]pyrimidin-1-ium-2-olate;or

M.UN.X.8:8-chloro-N-[2-chloro-5-methoxyphenyl)sulfonyl]-6-trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide;or

M.UN.X.9:4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide;or

M.UN.X.10:5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole.

The commercially available compounds of the group M listed above may befound in The Pesticide Manual, 15th Edition, C. D. S. Tomlin, BritishCrop Protection Council (2011) among other publications.

The quinoline derivative flometoquin is shown in WO 2006/013896. Theaminofuranone compounds flupyradifurone is known from WO 2007/115644.The sulfoximine compound sulfoxaflor is known from WO 2007/149134. Thepyrethroid momfluorothrin is known from U.S. Pat. No. 6,908,945. Thepyrazole acaricide pyflubumide is known from WO 2007/020986. Theisoxazoline compounds have been described likewise M.UN.X.1 in WO2005/085216, M.UN.X2. in WO 2009/002809 and in WO 2011/149749 and theisoxazoline M.UN.X.9 in WO 2013/050317. The pyripyropene derivativeafidopyropen has been described in WO 2006/129714. Thespiro-ketal-substituted cyclic ketoenol derivative M.UN.X.3 is knownfrom WO 2006/089633 and the biphenyl-substituted spirocyclic ketoenolderivative M.UN.X.4 from WO 2008/067911. Finally triazoylphenylsulfidelike M.UN.X.5 have been described in WO 2006/043635 and biologicalcontrol agents on basis of bacillus firmus in WO 2009/124707. Theneonicotionids 4A.1 is known from WO 20120/069266 and WO 2011/06946, theM.4.A.2 from WO 2013/003977, the M4.A.3. from WO 2010/069266.

The Metaflumizone analogue M.22C is described in CN 10171577. Thephthalamides M.28.1 and M.28.2 are both known from WO 2007/101540. Theanthranilamide M.28.3 has been described in WO 2005/077934. Thehydrazide compound M.28.4 has been described in WO 2007/043677. Theanthranilamides M.28.5a) to M.28.5h) can be prepared as described in WO2007/006670, WO 2013/024009 and WO 2013/024010, the anthranilamideM.28.5i) is described in WO 2011/085575, the M.28.5j) in WO 2008/134969,the M.28.5k) in US 2011/046186 and the M.28.5l) in WO 2012/034403. Thediamide compounds M.28.6 and M.28.7 can be found in CN 102613183.

The compounds M.UN.X.6a) to M.UN.X.6i) listed in M.UN.X.6 have beendescribed in WO 2012/029672. The mesoionic antagonist compound M.UN.X.7was described in WO 2012/092115, the nematicide M.UN.X.8 in WO2013/055584 and the Pyridalyl-type analogue M.UN.X.10 in WO 2010/060379.

In another embodiment of the invention, the compounds of formula (I), ortheir stereoisomers, salts, tautomers and N-oxides, may also be appliedwith fungicides as compound II.

The following list F of active substances, in conjunction with which thecompounds according to the invention can be used, is intended toillustrate the possible combinations but does not limit them:

F.I) Respiration Inhibitors

F.I-1) Inhibitors of complex III at Qo site:

strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin,dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl,metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin,pyrametostrobin, pyraoxystrobin, pyribencarb,triclopyricarb/chlorodincarb, trifloxystrobin,2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methylester and 2(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-Nmethyl-acetamide;

oxazolidinediones and imidazolinones: famoxadone, fenamidone;

F.I-2) Inhibitors of complex II (e.g. carboxamides):

carboxanilides: benodanil, benzovindiflupyr, bixafen, boscalid,carboxin, fenfuram, fenhexamid, fluopyram, flutolanil, furametpyr,isopyrazam, isotianil, mepronil, oxycarboxin, penflufen, penthiopyrad,sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4methyl-thiazole-5-carboxanilide, N-(3′,4′,5′ trifluorobiphenyl-2yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4 carboxamide (fluxapyroxad),N-(4′-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1-methyl-1Hpyrazole-4-carboxamide,N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5 fluoro-1H-pyrazole-4carboxamide,3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide;

F.I-3) Inhibitors of complex III at Qi site: cyazofamid, amisulbrom,[(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,[(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,[(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,[(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl2-methylpropanoate;

F.I-4) Other respiration inhibitors (complex I, uncouplers)diflumetorim;(5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine;tecnazen; ametoctradin; silthiofam; nitrophenyl derivates: binapacryl,dinobuton, dinocap, fluazinam, ferimzone, nitrthal-isopropyl, andincluding organometal compounds: fentin salts, such as fentin-acetate,fentin chloride or fentin hydroxide;

F.II) Sterol Biosynthesis Inhibitors (SBI Fungicides)

F.II-1) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles,imidazoles)

triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole,difenoconazole, diniconazole, diniconazole-M, epoxiconazole,fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole,imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole,penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole,tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole,1-[rel-(2S3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1H-[1,2,4]triazole,2-[re/(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol;

imidazoles: imazalil, pefurazoate, oxpoconazole, prochloraz,triflumizole;

pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox,triforine,1-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1H-[1,2,4]triazole,2-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol;

F.II-2) Delta14-reductase inhibitors (Amines, e.g. morpholines,piperidines)

morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph,tridemorph;

piperidines: fenpropidin, piperalin; spiroketalamines: spiroxamine;

F.II-3) Inhibitors of 3-keto reductase: hydroxyanilides: fenhexamid;

F.III) Nucleic Acid Synthesis Inhibitors

F.III-1) RNA, DNA synthesis

phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M,kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;

isoxazoles and iosothiazolones: hymexazole, octhilinone;

F.III-2) DNA topisomerase inhibitors: oxolinic acid;

F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase), hydroxy(2-amino)-pyrimidines: bupirimate;

F.IV) Inhibitors of Cell Division and or Cytoskeleton

F.IV-1) Tubulin inhibitors: benzimidazoles and thiophanates: benomyl,carbendazim, fuberidazole, thiabendazole, thiophanate-methyl;

triazolopyrimidines: 5-chloro-7(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5a]pyrimidine;

F.IV-2) Other cell division inhibitors

benzamides and phenyl acetamides: diethofencarb, ethaboxam, pencycuron,fluopicolide, zoxamide;

F.IV-3) Actin inhibitors: benzophenones: metrafenone; pyriofenone;

F.V) Inhibitors of Amino Acid and Protein Synthesis

F.V-1) Methionine synthesis inhibitors (anilino-pyrimidines)

anilino-pyrimidines: cyprodinil, mepanipyrim, nitrapyrin, pyrimethanil;

F.V-2) Protein synthesis inhibitors (anilino-pyrimidines)

antibiotics: blasticidin-S, kasugamycin, kasugamycinhydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin,polyoxine, validamycin A;

F.VI) Signal Transduction Inhibitors

F.VI-1) MAP/Histidine kinase inhibitors (e.g. anilino-pyrimidines)

dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;

phenylpyrroles: fenpiclonil, fludioxonil;

F.VI-2) G protein inhibitors: quinolines: quinoxyfen;

F.VII) Lipid and Membrane Synthesis Inhibitors

F.VII-1) Phospholipid biosynthesis inhibitors

organophosphorus compounds: edifenphos, iprobenfos, pyrazophos;

dithiolanes: isoprothiolane;

F.VII-2) Lipid peroxidation: aromatic hydrocarbons: dicloran,quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb,etridiazole;

F.VII-3) Carboxyl acid amides (CAA fungicides)

cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamid,pyrimorph;

valinamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb,valifenalate and N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl)carbamic acid-(4-fluorophenyl) ester;

F.VII-4) Compounds affecting cell membrane permeability and fatty acids:

1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,carbamates: propamocarb, propamocarbhydrochlorid,

F.VII-5) fatty acid amide hydrolase inhibitors:1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone;

F.VIII) Inhibitors with Multi Site Action

F.VIII-1) Inorganic active substances: Bordeaux mixture, copper acetate,copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

F.VIII-2) Thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam,methasulphocarb, metiram, propineb, thiram, zineb, ziram;

F.VIII-3) Organochlorine compounds (e.g. phthalimides, sulfamides,chloronitriles):

anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid,dichlorophen, flusulfamide, hexachlorobenzene, pentachlorphenole and itssalts, phthalide, tolylfluanid,N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methyl-benzenesulfonamide;

F.VIII-4) Guanidines and other: guanidine, dodine, dodine free base,guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate,iminoctadine-tris(albesilate),2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone;

F.VIII-5) Ahtraquinones: dithianon;

F.IX) Cell Wall Synthesis Inhibitors

F.IX-1) Inhibitors of glucan synthesis: validamycin, polyoxin B;

F.IX-2) Melanin synthesis inhibitors: pyroquilon, tricyclazole,carpropamide, dicyclomet, fenoxanil;

F.X) Plant Defence Inducers

F.X-1) Salicylic acid pathway: acibenzolar-S-methyl;

F.X-2) Others: probenazole, isotianil, tiadinil, prohexadione-calcium;

phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its salts;

F.XI) Unknown mode of action: bronopol, chinomethionat, cyflufenamid,cymoxanil, dazomet, debacarb, diclomezine, difenzoquat,difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover,flusulfamide, flutianil, methasulfocarb, nitrapyrin,nitrothal-isopropyl, oxathiapiprolin, oxin-copper, proquinazid,tebufloquin, tecloftalam, triazoxide,2-butoxy-6-iodo-3-propylchromen-4-one,N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenylacetamide,N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-Nmethyl formamidine, N′(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidine,N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine, N′-(5-difluoromethyl-2methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine,2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amide,2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide, methoxy-aceticacid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester andN-Methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolecarboxamide,3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine,pyrisoxazole,5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole-1carbothioic acid S-allyl ester, N-(6-methoxy-pyridin-3-yl)cyclopropanecarboxylic acid amide, 5-chloro-1(4,6-dimethoxypyrimidin-2-yl)-2-methyl-1H-benzoimidazole,2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxyacetamide;

F.XI) Growth regulators: abscisic acid, amidochlor, ancymidol,6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequatchloride), choline chloride, cyclanilide, daminozide, dikegulac,dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol,fluthiacet, forchlorfenuron, gibberellic acid, inabenfide,indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquatchloride), naphthaleneacetic acid, N 6-benzyladenine, paclobutrazol,prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron,triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri iodobenzoic acid,trinexapac-ethyl and uniconazole;

F.XII) Biological Control Agents

Ampelomyces quisqualis (e.g. AQ 10® from Intrachem Bio GmbH & Co. KG,Germany), Aspergillus flavus (e.g. AFLAGUARD® from Syngenta, CH),Aureobasidium pullulans (e.g. BO-TECTOR® from bio-ferm GmbH, Germany),Bacillus pumilus (e.g. NRRL Accession No. B-30087 in SONATA® and BALLAD®Plus from AgraQuest Inc., USA), Bacillus subtilis (e.g. isolate NRRL-Nr.B-21661 in RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuestInc., USA), Bacillus subtilis var. amyloliquefaciens FZB24 (e.g. TAEGRO®from Novozyme Biologicals, Inc., USA), Candida oleophila 1-82 (e.g.ASPIRE® from Ecogen Inc., USA), Candida saitoana (e.g. BIOCURE® (inmixture with lysozyme) and BIOCOAT® from Micro Flo Company, USA (BASFSE) and Arysta), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., NZ),Clonostachys rosea f. catenulata, also named Gliocladium catenulatum(e.g. isolate J1446: PRESTOP® from Verdera, Finland), Coniothyriumminitans (e.g. CONTANS® from Prophyta, Germany), Cryphonectriaparasitica (e.g. Endothia parasitica from CNICM, France), Cryptococcusalbidus (e.g. YIELD PLUS® from Anchor Bio-Technologies, South Africa),Fusarium oxysporum (e.g. BIOFOX® from S.I.A.P.A., Italy, FUSACLEAN® fromNatural Plant Protection, France), Metschnikowia fructicola (e.g.SHEMER® from Agrogreen, Israel), Microdochium dimerum (e.g. ANTIBOT®from Agrauxine, France), Phlebiopsis gigantea (e.g. ROTSOP® fromVerdera, Finland), Pseudozyma flocculosa (e.g. SPORODEX® from PlantProducts Co. Ltd., Canada), Pythium oligandrum DV74 (e.g. POLYVERSUM®from Remeslo SSRO, Biopreparaty, Czech Rep.), Reynoutria sachlinensis(e.g. REGALIA® from Marrone BioInnovations, USA), Talaromyces flavusV117b (e.g. PROTUS® from Prophyta, Germany), Trichoderma asperellumSKT-1 (e.g. ECO-HOPE® from Kumiai Chemical Industry Co., Ltd., Japan),T. atroviride LC52 (e.g. SENTINEL® from Agrimm Technologies Ltd, NZ), T.harzianum T-22 (e.g. PLANTSHIELD® der Firma BioWorks Inc., USA), T.harzianum TH 35 (e.g. ROOT PRO® from Mycontrol Ltd., Israel), T.harzianum T-39 (e.g. TRICHODEX® and TRICHODERMA 2000® from MycontrolLtd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride(e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum ICC012and T. viride ICC080 (e.g. REMEDIER® WP from Isagro Ricerca, Italy), T.polysporum and T. harzianum (e.g. BINAB® from BINAB Bio-Innovation AB,Sweden), T. stromaticum (e.g. TRICOVAB® from C.E.P.L.A.C., Brazil), T.virens GL-21 (e.g. SOILGARD® from Certis LLC, USA), T. viride (e.g.TRIECO® from Ecosense Labs. (India) Pvt. Ltd., Indien, BIO-CURE® F fromT. Stanes & Co. Ltd., Indien), T. viride TV1 (e.g. T. viride TV1 fromAgribiotec srl, Italy), Ulocladium oudemansii HRU3 (e.g. BOTRY-ZEN® fromBotry-Zen Ltd, NZ).

The commercially available compounds II of the group F listed above maybe found in The Pesticide Manual, 15th Edition, C. D. S. Tomlin, BritishCrop Protection Council (2011) among other publications. Theirpreparation and their activity against harmful fungi is known (cf.:http://www.alanwood.net/pesticides/); these substances are commerciallyavailable. The compounds described by IUPAC nomenclature, theirpreparation and their fungicidal activity are also known (cf. Can. J.Plant Sci. 48(6), 587-94, 1968; EP A 141 317; EP-A 152 031; EP A 226917; EP A 243 970; EP A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028125; EP-A 1 035 122; EP A 1 201 648; EP A 1 122 244, JP 2002316902; DE19650197; DE 10021412; DE 102005009458; U.S. Pat. No. 3,296,272; U.S.Pat. No. 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783;WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO06/87343; WO 07/82098; WO 07/90624, WO 11/028657).

The invertebrate pest, e.g. the insects, arachnids and nematodes, theplant, soil or water in which the plant is growing can be contacted withthe present compounds of formula (I), including their stereoisomers andtautomers, as well the salts thereof, or composition(s) containing themby any application method known in the art. As such, “contacting”includes both direct contact (applying the compounds/compositionsdirectly on the animal pest or plant—typically to the foliage, stem orroots of the plant) and indirect contact (applying thecompounds/compositions to the locus of the animal pest or plant).

The compounds of formula (I), including their stereoisomers andtautomers, as well the salts thereof, or the pesticidal compositionscomprising them may be used to protect growing plants and crops fromattack or infestation by animal pests, especially insects, acaridae orarachnids by contacting the plant/crop with a pesticidally effectiveamount of compounds of formula (I). The term “crop” refers both togrowing and harvested crops.

The compounds of the present invention and the compositions comprisingthem are particularly important in the control of a multitude of insectson various cultivated plants, such as cereal, root crops, oil crops,vegetables, spices, ornamentals, for example seed of durum and otherwheat, barley, oats, rye, maize (fodder maize and sugar maize/sweet andfield corn), soybeans, oil crops, crucifers, cotton, sunflowers,bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet,eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks,pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons,Brassica species, melons, beans, peas, garlic, onions, carrots, tuberousplants such as potatoes, sugar cane, tobacco, grapes, petunias,geranium/pelargoniums, pansies and impatiens.

The compounds of the present invention are employed as such or in formof compositions by treating the insects or the plants, plant propagationmaterials, such as seeds, soil, surfaces, materials or rooms to beprotected from insecticidal attack with a insecticidally effectiveamount of the active compounds. The application can be carried out bothbefore and after the infection of the plants, plant propagationmaterials, such as seeds, soil, surfaces, materials or rooms by theinsects.

The present invention also includes a method of combating animal pestswhich comprises contacting the animal pests, their habit, breedingground, food supply, cultivated plants, seed, soil, area, material orenvironment in which the animal pests are growing or may grow, or thematerials, plants, seeds, soils, surfaces or spaces to be protected fromanimal attack or infestation with a pesticidally effective amount of atleast one active compound of the formula (I), a stereoisomers, atautomere or a salt thereof.

Moreover, animal pests may be controlled by contacting the target pest,its food supply, habitat, breeding ground or its locus with apesticidally effective amount of compounds of formula (I), astereoisomer, a tautomere or a salt thereof. As such, the applicationmay be carried out before or after the infection of the locus, growingcrops, or harvested crops by the pest.

The compounds of the invention can also be applied preventively toplaces at which occurrence of the pests is expected.

The compounds of formula (I), including their stereoisomers and theirtautomers, as well as their salts may be also used to protect growingplants from attack or infestation by pests. The use includes contactingthe plant with a pesticidally effective amount of compounds of formula(I), a stereoisomer, a tautomere or a salt thereof. As such,“contacting” includes both direct contact, i.e. applying thecompounds/compositions directly on the pest and/or plant—typically tothe foliage, stem or roots of the plant, and indirect contact, i.e.applying the compounds/compositions to the locus of the pest and/orplant.

“Locus” means a habitat, breeding ground, plant, seed, soil, area,material or environment in which a pest or parasite is growing or maygrow.

The term “plant propagation material” is to be understood to denote allthe generative parts of the plant such as seeds and vegetative plantmaterial such as cuttings and tubers (e.g. potatoes), which can be usedfor the multiplication of the plant. This includes seeds, roots, fruits,tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants.Seedlings and young plants, which are to be transplanted aftergermination or after emergence from soil, may also be included. Theseplant propagation materials may be treated prophylactically with a plantprotection compound either at or before planting or transplanting.

The term “cultivated plants” is to be understood as including plantswhich have been modified by breeding, mutagenesis or geneticengineering. Genetically modified plants are plants, which geneticmaterial has been so modified by the use of recombinant DNA techniquesthat under natural circumstances cannot readily be obtained by crossbreeding, mutations or natural recombination. Typically, one or moregenes have been integrated into the genetic material of a geneticallymodified plant in order to improve certain properties of the plant. Suchgenetic modifications also include but are not limited to targetedpost-transtional modification of protein(s) (oligo- or polypeptides)poly for example by glycosylation or polymer additions such asprenylated, acetylated or farnesylated moieties or PEG moieties (e.g. asdisclosed in Biotechnol Prog. 2001 July-August; 17(4):720-8., ProteinEng Des Sel. 2004 January; 17(1):57-66, Nat Protoc. 2007; 2(5):1225-35.,Curr Opin Chem Biol. 2006 October; 10(5):487-91. Epub 2006 Aug. 28.,Biomaterials. 2001 March; 22(5):405-17, Bioconjug Chem. 2005January-February; 16(1):113-21).

The term “cultivated plants” is to be understood also including plantsthat have been rendered tolerant to applications of specific classes ofherbicides, such as hydroxy-phenylpyruvate dioxygenase (HPPD)inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonylureas (see e.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (seee.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphatesynthase (EPSPS) inhibitors, such as glyphosate (see e.g. WO 92/00377);glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g.EP-A-0242236, EP-A-242246) or oxynil herbicides (see e.g. U.S. Pat. No.5,559,024) as a result of conventional methods of breeding or geneticengineering. Several cultivated plants have been rendered tolerant toherbicides by conventional methods of breeding (mutagenesis), forexample Clearfield® summer rape (Canola) being tolerant toimidazolinones, e.g. imazamox. Genetic engineering methods have beenused to render cultivated plants, such as soybean, cotton, corn, beetsand rape, tolerant to herbicides, such as glyphosate and glufosinate,some of which are commercially available under the trade namesRoundupReady® (glyphosate) and LibertyLink® (glufosinate).

The term “cultivated plants” is to be understood also including plantsthat are by the use of recombinant DNA techniques capable to synthesizeone or more insecticidal proteins, especially those known from thebacterial genus Bacillus, particularly from Bacillus thuringiensis, suchas ä-endotoxins, e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b),CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP),e.g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteriacolonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.;toxins produced by animals, such as scorpion toxins, arachnid toxins,wasp toxins, or other insect-specific neurotoxins; toxins produced byfungi, such Streptomycetes toxins, plant lectins, such as pea or barleylectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors,serine protease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilben synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as pre-toxins,hybrid proteins, truncated or otherwise modified proteins. Hybridproteins are characterized by a new combination of protein domains,(see, for example WO 02/015701). Further examples of such toxins orgenetically-modified plants capable of synthesizing such toxins aredis-closed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656,EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073. The methodsfor producing such genetically modified plants are generally known tothe person skilled in the art and are described, for example, in thepublications mentioned above. These insecticidal proteins contained inthe genetically modified plants impart to the plants producing theseproteins protection from harmful pests from certain taxonomic groups ofarthropods, particularly to beetles (Coleoptera), flies (Diptera), andbutterflies and moths (Lepidoptera) and to plant parasitic nematodes(Nematoda).

The term “cultivated plants” is to be understood also including plantsthat are, e.g. by the use of recombinant DNA techniques, capable ofsynthesizing one or more proteins in order to increase the resistance ortolerance of those plants to bacterial, viral or fungal pathogens.Examples of such proteins are the so-called “pathogenesis-relatedproteins”, also termed PR proteins—see, for example EP-A 0 392 225—, orplant disease resistance genes—for example potato cultivars, whichexpress resistance genes acting against Phytophthora infestans derivedfrom the mexican wild potato Solanum bulbocastanum—or T4-lysozym—e.g.potato cultivars capable of synthesizing these proteins with increasedresistance against bacteria such as Erwinia amylvora. The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, for example, in thepublications mentioned above.

The term “cultivated plants” is to be understood also including plantsthat are, e.g. by the use of recombinant DNA techniques, capable ofsynthesizing one or more proteins to increase the productivity, e.g. biomass production, grain yield, starch content, oil content or proteincontent, or to improve tolerance to drought, salinity or othergrowth-limiting environmental factors or tolerance to pests and fungal,bacterial or viral pathogens of those plants.

The term “cultivated plants” is to be understood also including plantsthat contain by the use of recombinant DNA techniques a modified amountof substances of content or new substances of content, specifically toimprove human or animal nutrition, for example oil crops that producehealth-promoting long-chain omega-3 fatty acids or unsaturated omega-9fatty acids (e.g. Nexera® rape).

The term “cultivated plants” is to be understood also including plantsthat contain by the use of recombinant DNA techniques a modified amountof substances of content or new substances of content, specifically toimprove raw material production, for example potatoes that produceincreased amounts of amylopectin (e.g. Amflora® potato).

In general, “pesticidally effective amount” means the amount of activeingredient needed to achieve an observable effect on growth, includingthe effects of necrosis, death, retardation, prevention, and removal,destruction, or otherwise diminishing the occurrence and activity of thetarget organism. The pesticidally effective amount can vary for thevarious compounds/compositions used in the invention. A pesticidallyeffective amount of the compositions will also vary according to theprevailing conditions such as desired pesticidal effect and duration,weather, target species, locus, mode of application, and the like.

In the case of soil treatment or of application to the pests dwellingplace or nest, the quantity of active ingredient ranges from 0.0001 to500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

Customary application rates in the protection of materials are, forexample, from 0.01 g to 1000 g of active compound per m² treatedmaterial, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materialstypically contain from 0.001 to 95 weight %, preferably from 0.1 to 45weight %, and more preferably from 1 to 25 weight % of at least onerepellent and/or insecticide.

For use in treating crop plants, the rate of application of the activeingredients of this invention may be in the range of 0.1 g to 4000 g perhectare, desirably from 25 g to 600 g per hectare, more desirably from50 g to 500 g per hectare.

The compounds of formula (I), including the tautomers and stereoisomers,as well as their salts, are effective through both contact, e.g. viasoil, glass, wall, bed net, carpet, plant parts or animal parts, andingestion, e.g. via ingestion of bait or plant part.

The compounds of the invention may also be applied against non-cropinsect pests, such as ants, termites, wasps, flies, mosquitos, crickets,or cockroaches. For use against said non-crop pests, compounds offormula (I), including the tautomers and stereoisomers, as well as theirsalts, are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. agel). Solid baits can be formed into various shapes and forms suitableto the respective application e.g. granules, blocks, sticks, disks.Liquid baits can be filled into various devices to ensure properapplication, e.g. open containers, spray devices, droplet sources, orevaporation sources. Gels can be based on aqueous or oily matrices andcan be formulated to particular necessities in terms of stickyness,moisture retention or aging characteristics.

The bait employed in the composition is a product, which is sufficientlyattractive to incite insects such as ants, termites, wasps, flies,mosquitos, crickets etc. or cockroaches to eat it. The attractivenesscan be manipulated by using feeding stimulants or sex pheromones. Foodstimulants are chosen, for example, but not exclusively, from animaland/or plant proteins (meat-, fish- or blood meal, insect parts, eggyolk), from fats and oils of animal and/or plant origin, or mono-,oligo- or polyorganosaccharides, especially from sucrose, lactose,fructose, dextrose, glucose, starch, pectin or even molasses or honey.Fresh or decaying parts of fruits, crops, plants, animals, insects orspecific parts thereof can also serve as a feeding stimulant. Sexpheromones are known to be more insect specific. Specific pheromones aredescribed in the literature and are known to those skilled in the art.

For use in bait compositions, the typical content of active ingredientis from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to5% weight % of active compound.

Formulations of compounds of formula (I), including the tautomers andstereoisomers, as well as their salts, as aerosols, e.g in spray cans,oil sprays or pump sprays are highly suitable for the non-professionaluser for controlling pests such as flies, fleas, ticks, mosquitos orcockroaches. Aerosol recipes are preferably composed of the activecompound, solvents such as lower alcohols, e.g. methanol, ethanol,propanol or butanol, ketones, e.g. acetone, methyl ethyl ketone,paraffin hydrocarbons, e.g. kerosenes or mineral oils, having boilingranges of approximately 50 to 250° C., dimethylformamide,N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such astoluene, xylene, water, furthermore auxiliaries such as emulsifiers suchas sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethyleneoxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils,esters of medium fatty acids with lower alcohols, aromatic carbonylcompounds, if appropriate stabilizers such as sodium benzoate,amphoteric surfactants, lower epoxides, triethyl orthoformate and, ifrequired, propellants such as propane, butane, nitrogen, compressed air,dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of thesegases.

The oil spray formulations differ from the aerosol recipes in that nopropellants are used.

For use in spray compositions, the content of active ingredient is from0.001 to 80 weights %, preferably from 0.01 to 50 weight % and mostpreferably from 0.01 to 15 weight %.

The compounds of formula (I), including the tautomers and stereoisomers,as well as their salts, and their respective compositions can also beused in mosquito and fumigating coils, smoke cartridges, vaporizerplates or long-term vaporizers and also in moth papers, moth pads orother heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects, such asmalaria, dengue and yellow fever, lymphatic filariasis, andleishmaniasis, with compounds of formula (I) or the stereoisomers,tautomers or salts thereof, and with their respective compositions alsocomprise treating surfaces of huts and houses, air spraying andimpregnation of curtains, tents, clothing items, bed nets, tsetse-flytrap or the like. Insecticidal compositions for application to fibers,fabric, knitgoods, nonwovens, netting material or foils and tarpaulinspreferably comprise a mixture including the insecticide, optionally arepellent and at least one binder. Suitable repellents for example areN,N-Diethyl-meta-toluamide (DEET), N,N-diethylphenylacetamide (DEPA),1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine,(2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1,3-hexandiol,indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insectcontrol such as{(+/−)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate(Esbiothrin), a repellent derived from or identical with plant extractslike limonene, eugenol, (+)-Eucamalol (1), (−)-1-epi-eucamalol or crudeplant extracts from plants like Eucalyptus maculata, Vitex rotundifolia,Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogannartdus (citronella). Suitable binders are selected for example frompolymers and copolymers of vinyl esters of aliphatic acids (such as suchas vinyl acetate and vinyl versatate), acrylic and methacrylic esters ofalcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methylacrylate, mono- and di-ethylenically unsaturated hydrocarbons, such asstyrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dippingthe textile material into emulsions or dispersions of the insecticide orspraying them onto the nets.

The compounds of formula (I), including the tautomers and stereoisomers,as well as their salts, and their compositions can be used forprotecting wooden materials such as trees, board fences, sleepers, etc.and buildings such as houses, outhouses, factories, but alsoconstruction materials, furniture, leathers, fibers, vinyl articles,electric wires and cables etc. from ants and/or termites, and forcontrolling ants and termites from doing harm to crops or human being,e.g. when the pests invade into houses and public facilities. Thecompounds of formula (I), their stereoisomers, their tautomers or theirsalts are applied not only to the surrounding soil surface or into theunder-floor soil in order to protect wooden materials but it can also beapplied to lumbered articles such as surfaces of the under-floorconcrete, alcove posts, beams, plywoods, furniture, etc., woodenarticles such as particle boards, half boards, etc. and vinyl articlessuch as coated electric wires, vinyl sheets, heat insulating materialsuch as styrene foams, etc. In case of application against ants doingharm to crops or human beings, the ant controller of the presentinvention is applied to the crops or the surrounding soil, or isdirectly applied to the nest of ants or the like.

The compounds of formula (I), including the tautomers and stereoisomers,as well as their salts, are also suitable for the treatment of seeds inorder to protect the seed from insect pest, in particular fromsoil-living insect pests and the resulting plant's roots and shootsagainst soil pests and foliar insects.

The compounds of formula (I), including the tautomers and stereoisomers,as well as their salts, are particularly useful for the protection ofthe seed from soil pests and the resulting plant's roots and shootsagainst soil pests and foliar insects. The protection of the resultingplant's roots and shoots is preferred. More preferred is the protectionof resulting plant's shoots from piercing and sucking insects, whereinthe protection from aphids is most preferred.

The present invention therefore comprises a method for the protection ofseeds from insects, in particular from soil insects and of theseedling's roots and shoots from insects, in particular from soil andfoliar insects, said method comprising contacting the seeds beforesowing and/or after pregermination with a compound of the generalformula (I), a tautomer, a stereoisomer or a salt thereof. Particularlypreferred is a method, wherein the plant's roots and shoots areprotected, more preferably a method, wherein the plants shoots areprotected form piercing and sucking insects, most preferably a method,wherein the plants shoots are protected from aphids.

The term seed includes seeds and plant propagules of all kinds includingbut not limited to true seeds, seed pieces, suckers, corms, bulbs,fruit, tubers, grains, cuttings, cut shoots and the like and means in apreferred embodiment true seeds.

The term seed treatment includes all suitable seed treatment techniquesknown in the art, such as seed dressing, seed coating, seed dusting,seed soaking and seed pelleting.

The present invention also relates to seeds coated with or containingthe active compound of the present invention, i.e. containing a compoundof formula (I), a stereoisomer, a tautomer or a salt thereof.

The term “coated with and/or containing” generally signifies that theactive ingredient is for the most part on the surface of the propagationproduct at the time of application, although a greater or lesser part ofthe ingredient may penetrate into the propagation product, depending onthe method of application. When the said propagation product is(re)planted, it may absorb the active ingredient.

Suitable seed is seed of cereals, root crops, oil crops, vegetables,spices, ornamentals, for example seed of durum and other wheat, barley,oats, rye, maize (fodder maize and sugar maize/sweet and field corn),soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice,oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes,grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash,cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species,melons, beans, peas, garlic, onions, carrots, tuberous plants such aspotatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums,pansies and impatiens.

In addition, the compounds of formula (I), including the tautomers andstereoisomers, as well as their salts, may also be used for thetreatment seeds from plants, which tolerate the action of herbicides orfungicides or insecticides owing to breeding, including geneticengineering methods.

For example, the compounds of formula (I), including the tautomers andstereoisomers, as well as their salts, can be employed in treatment ofseeds from plants, which are resistant to herbicides from the groupconsisting of the sulfonylureas, imidazolinones, glufosinateammonium orglyphosate-isopropylammonium and analogous active substances (see forexample, EP-A-0242236, EP-A-242246) (WO 92/00377) (EP-A-0257993, U.S.Pat. No. 5,013,659) or in transgenic crop plants, for example cotton,with the capability of producing Bacillus thuringiensis toxins (Bttoxins) which make the plants resistant to certain pests (EP-A-0142924,EP-A-0193259),

Furthermore, the compounds of formula (I), including the tautomers andstereoisomers, as well as their salts, can be used also for thetreatment of seeds from plants, which have modified characteristics incomparison with existing plants consist, which can be generated forexample by traditional breeding methods and/or the generation ofmutants, or by recombinant procedures). For example, a number of caseshave been described of recombinant modifications of crop plants for thepurpose of modifying the starch synthesized in the plants (e.g. WO92/11376, WO 92/14827, WO 91/19806) or of transgenic crop plants havinga modified fatty acid composition (WO 91/13972).

The seed treatment application of the active compound is carried out byspraying or by dusting the seeds before sowing of the plants and beforeemergence of the plants.

Compositions which are especially useful for seed treatment are e.g.:

A Soluble concentrates (SL, LS)

D Emulsions (EW, EO, ES)

E Suspensions (SC, OD, FS)

F Water-dispersible granules and water-soluble granules (WG, SG)

G Water-dispersible powders and water-soluble powders (WP, SP, WS)

H Gel-Formulations (GF)

I Dustable powders (DP, DS)

Conventional seed treatment formulations include for example flowableconcentrates FS, solutions LS, powders for dry treatment DS, waterdispersible powders for slurry treatment WS, water-soluble powders SSand emulsion ES and EC and gel formulation GF. These formulations can beapplied to the seed diluted or undiluted. Application to the seeds iscarried out before sowing, either directly on the seeds or after havingpregerminated the latter

In a preferred embodiment a FS formulation is used for seed treatment.Typically, a FS formulation may comprise 1-800 g/l of active ingredient,1-200 g/l Surfactant, 0 to 200 g/l anti-freezing agent, 0 to 400 g/l ofbinder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent,preferably water.

Especially preferred FS formulations of a compound of formula (I), astereoisomer, a tautomer or a salt, for seed treatment usually comprisefrom 0.1 to 80% by weight (1 to 800 g/l) of the compound of formula (I),including its tautomers and stereoisomers, or a salt thereof, from 0.1to 20% by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to5% by weight of a wetter and from 0.5 to 15% by weight of a dispersingagent, up to 20% by weight, e.g. from 5 to 20% of an anti-freeze agent,from 0 to 15% by weight, e.g. 1 to 15% by weight of a pigment and/or adye, from 0 to 40% by weight, e.g. 1 to 40% by weight of a binder(sticker/adhesion agent), optionally up to 5% by weight, e.g. from 0.1to 5% by weight of a thickener, optionally from 0.1 to 2% of ananti-foam agent, and optionally a preservative such as a biocide,antioxidant or the like, e.g. in an amount from 0.01 to 1% by weight anda filler/vehicle up to 100% by weight.

Seed Treatment formulations may additionally also comprise binders andoptionally colorants.

Binders can be added to improve the adhesion of the active materials onthe seeds after treatment. Suitable binders are homo- and copolymersfrom alkylene oxides like ethylene oxide or propylene oxide,polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, andcopolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- andcopolymers, polyethyleneamines, polyethyleneamides andpolyethyleneimines, polysaccharides like celluloses, tylose and starch,polyolefin homo- and copolymers like olefin/maleic anhydride copolymers,polyurethanes, polyesters, polystyrene homo and copolymers

Optionally, also colorants can be included in the formulation. Suitablecolorants or dyes for seed treatment formulations are Rhodamin B, C.I.Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigmentyellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigmentred 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigmentorange 34, pigment orange 5, pigment green 36, pigment green 7, pigmentwhite 6, pigment brown 25, basic violet 10, basic violet 49, acid red51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10,basic red 108.

Examples of a gelling agent is carrageen (Satiagel®)

In the treatment of seed, the application rates of the compounds offormula (I) are generally from 0.1 g to 10 kg per 100 kg of seed,preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 gto 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100kg of seed.

The invention therefore also relates to seed comprising a compound ofthe formula (I), a tautomer, a stereoisomer or an agriculturally usefulsalt thereof, as defined herein. The amount of the compound of theformula (I) or the agriculturally useful salt thereof will in generalvary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kgper 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed.For specific crops such as lettuce the rate can be higher.

The compounds of formula (I), including their stereoisomers and theirtautomers, and the veterinarily acceptable salts thereof are inparticular also suitable for being used for combating parasites in andon animals.

An object of the present invention is therfore also to provide newmethods to control parasites in and on animals. Another object of theinvention is to provide safer pesticides for animals. Another object ofthe invention is further to provide pesticides for animals that may beused in lower doses than existing pesticides. And another object of theinvention is to provide pesticides for animals, which provide a longresidual control of the parasites.

The invention also relates to compositions containing a parasiticallyeffective amount of a compound of formula (I) or a stereoisomer or atautomer or a veterinarily acceptable salt thereof and an acceptablecarrier, for combating parasites in and on animals.

The present invention also provides a method for treating, controlling,preventing and protecting animals against infestation and infection byparasites, which comprises orally, topically or parenterallyadministering or applying to the animals a parasitically effectiveamount of a compound of formula (I) or a stereoisomer or a tautomer or aveterinarily acceptable salt thereof or a composition comprising it.

The invention also provides a process for the preparation of acomposition for treating, controlling, preventing or protecting animalsagainst infestation or infection by parasites which comprises aparasitically effective amount of a compound of formula (I) or astereoisomer or a tautomer or a veterinarily acceptable salt thereof ora composition comprising it.

Activity of compounds against agricultural pests does not suggest theirsuitability for control of endo- and ectoparasites in and on animalswhich requires, for example, low, non-emetic dosages in the case of oralapplication, metabolic compatibility with the animal, low toxicity, anda safe handling.

Surprisingly it has now been found that compounds of formula (I),including their stereoisomers and tautomers, and the salts thereof, aresuitable for combating endo- and ectoparasites in and on animals.

Compounds of formula (I), including their stereoisomers and theirtautomers, and the veterinarily acceptable salts thereof, andcompositions comprising them are preferably used for controlling andpreventing infestations and infections animals including warm-bloodedanimals, including humans, and fish. They are for example suitable forcontrolling and preventing infestations and infections in mammals suchas cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits,goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer,and also in fur-bearing animals such as mink, chinchilla and raccoon,birds such as hens, geese, turkeys and ducks and fish such as fresh- andsalt-water fish such as trout, carp and eels.

Compounds of formula (I), including their stereoisomers and theirtautomers, and the veterinarily acceptable salts thereof andcompositions comprising them are preferably used for controlling andpreventing infestations and infections in domestic animals, such as dogsor cats.

Infestations in warm-blooded animals and fish include, but are notlimited to, lice, biting lice, ticks, nasal bots, keds, biting flies,muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoesand fleas.

The compounds of formula (I), including their stereoisomers and theirtautomers, and the veterinarily acceptable salts thereof andcompositions comprising them are suitable for systemic and/ornon-systemic control of ecto- and/or endoparasites. They are activeagainst all or some stages of development.

The compounds of formula (I) including their stereoisomers and theirtautomers, and the veterinarily acceptable salts thereof are especiallyuseful for combating ectoparasites.

The compounds of formula (I), including their stereoisomers and theirtautomers, and the veterinarily acceptable salts thereof are especiallyuseful for combating parasites of the following orders and species,respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis,Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllusfasciatus;

cockroaches (Blattaria-Blattodea), e.g. Battella germanica, Battellaasahinae, Periplaneta americana, Periplaneta japonica, Periplanetabrunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blattaorientalis;

-   -   flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes        albopictus, Aedes vexans, Anastrepha ludens, Anopheles        maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles        gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles        minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya        bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops        discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia        hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex        pipiens, Culex nigripalpus, Culex quinque-fasciatus, Culex        tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia        hominis, Fannia canicularis, Gasterophilus intestinalis,        Glossina morsitans, Glossina palpalis, Glossina fuscipes,        Glossina tachinoides, Haematobia irritans, Haplodiplosis        equestris, Hippelates spp., Hypoderma lineata, Leptoconops        torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata,        Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina        stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora        columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga        haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys        calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola,        and Tabanus similis,

lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanuscorporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis,Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthusstramineus and Solenopotes capillatus;

ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodesscapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalussanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyommaamericanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorusturicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacotiand Dermanyssus gallinae;

Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp.,Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp.,Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.,Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp.,Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.,Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptesspp;

Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduviussenilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arliuscritatus;

Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp.,Phtirus spp., and Solenopotes spp.;

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenoponspp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp.,Lepikentron spp., Trichodectes spp., and Felicola spp;

Roundworms Nematoda:

Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae(Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp.;

Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp;

Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus,Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchuscontortus., Ostertagia spp., Cooperia spp., Nematodirus spp.,Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurusdentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamustrachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necatorspp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp.,Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylusabstrusus, and Dioctophyma renale;

Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascarissuum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis(Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., andOxyuris equi;

Camallanida, e.g. Dracunculus medinensis (guinea worm);

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocercaspp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophoraspp., Spirocerca lupi, and Habronema spp.;

Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp.,Macracanthorhynchus hirudinaceus and Oncicola spp;

Planarians (Plathelminthes):

Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimusspp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis,Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp.,and Nanocyetes spp;

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g.Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidiumcaninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp.,Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp.,Anoplocephala spp., and Hymenolepis spp.

The compounds of formula (I), including their stereoisomers and theirtautomers, and the salts thereof and compositions containing them areparticularly useful for the control of pests from the orders Diptera,Siphonaptera and Ixodida.

Moreover, the use of the compounds of formula (I), including theirstereoisomers and their tautomers, and the salts thereof andcompositions containing them for combating mosquitoes is especiallypreferred.

The use of the compounds of formula (I), including their stereoisomersand their tautomers, and the salts thereof and compositions containingthem for combating flies is a further preferred embodiment of thepresent invention.

Furthermore, the use of the compounds of formula (I), including theirstereoisomers and their tautomers, and the salts thereof andcompositions containing them for combating fleas is especiallypreferred.

The use of the compounds of formula (I), including their stereoisomersand their tautomers, and the salts thereof and compositions containingthem for combating ticks is a further preferred embodiment of thepresent invention.

The compounds of formula (I), including their stereoisomers and theirtautomers, and the salts thereof also are especially useful forcombating endoparasites (roundworms nematoda, thorny headed worms andplanarians).

Administration can be carried out both prophylactically andtherapeutically.

Administration of the active compounds is carried out directly or in theform of suitable preparations, orally, topically/dermally orparenterally.

For oral administration to warm-blooded animals, the compounds of thepresent invention may be formulated as animal feeds, animal feedpremixes, animal feed concentrates, pills, solutions, pastes,suspensions, drenches, gels, tablets, boluses and capsules. In addition,the compounds of the present invention may be administered to theanimals in their drinking water. For oral administration, the dosageform chosen should provide the animal with 0.01 mg/kg to 100 mg/kg ofanimal body weight per day of the formula (I) compound, preferably with0.5 mg/kg to 100 mg/kg of animal body weight per day.

Alternatively, the compounds of the present invention may beadministered to animals parenterally, for example, by intraruminal,intramuscular, intravenous or subcutaneous injection. The compounds ofthe present invention may be dispersed or dissolved in a physiologicallyacceptable carrier for subcutaneous injection. Alternatively, thecompounds of the present invention may be formulated into an implant forsubcutaneous administration. In addition the compounds of the presentinvention may be transdermally administered to animals. For parenteraladministration, the dosage form chosen should provide the animal with0.01 mg/kg to 100 mg/kg of animal body weight per day of a compound ofthe present invention.

The compounds of the present invention may also be applied topically tothe animals in the form of dips, dusts, powders, collars, medallions,sprays, shampoos, spot-on and pour-on formulations and in ointments oroil-in-water or water-in-oil emulsions. For topical application, dipsand sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to3,000 ppm of the compounds of the present invention. In addition, thecompounds of the present invention may be formulated as ear tags foranimals, particularly quadrupeds such as cattle and sheep.

Suitable preparations are:

-   -   Solutions such as oral solutions, concentrates for oral        administration after dilution, solutions for use on the skin or        in body cavities, pouring-on formulations, gels;    -   Emulsions and suspensions for oral or dermal administration;        semi-solid preparations;    -   Formulations in which the active compound is processed in an        ointment base or in an oil-in-water or water-in-oil emulsion        base;    -   Solid preparations such as powders, premixes or concentrates,        granules, pellets, tablets, boluses, capsules; aerosols and        inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving theactive ingredient in a suitable solvent and optionally adding furtheringredients such as acids, bases, buffer salts, preservatives, andsolubilizers. The solutions are filtered and filled sterile.

Suitable solvents are physiologically tolerable solvents such as water,alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propyleneglycol, polyethylene glycols, N-methyl-pyrrolidone, 2-pyrrolidone, andmixtures thereof.

The compounds of the present invention can optionally be dissolved inphysiologically tolerable vegetable or synthetic oils which are suitablefor injection.

Suitable solubilizers are solvents which promote the dissolution of theactive compound in the main solvent or prevent its precipitation.Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylatedcastor oil, and polyoxyethylated sorbitan ester.

Suitable preservatives are benzyl alcohol, trichlorobutanol,p-hydroxybenzoic acid esters, and n-butanol.

Oral solutions are administered directly. Concentrates are administeredorally after prior dilution to the use concentration. Oral solutions andconcentrates are prepared according to the state of the art and asdescribed above for injection solutions, sterile procedures not beingnecessary.

Solutions for use on the skin are trickled on, spread on, rubbed in,sprinkled on or sprayed on.

Solutions for use on the skin are prepared according to the state of theart and according to what is described above for injection solutions,sterile procedures not being necessary.

Further suitable solvents are polypropylene glycol, phenyl ethanol,phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate,ethers such as alkyleneglycol alkylether, e.g. dipropylenglycolmonomethylether, ketons such as acetone, methylethylketone, aromatichydrocarbons, vegetable and synthetic oils, dimethylformamide,dimethylacetamide, transcutol, solketal, propylencarbonate, and mixturesthereof.

It may be advantageous to add thickeners during preparation. Suitablethickeners are inorganic thickeners such as bentonites, colloidalsilicic acid, aluminium monostearate, organic thickeners such ascellulose derivatives, polyvinyl alcohols and their copolymers,acrylates and methacrylates.

Gels are applied to or spread on the skin or introduced into bodycavities. Gels are prepared by treating solutions which have beenprepared as described in the case of the injection solutions withsufficient thickener that a clear material having an ointment-likeconsistency results. The thickeners employed are the thickeners givenabove.

Pour-on formulations are poured or sprayed onto limited areas of theskin, the active compound penetrating the skin and acting systemically.

Pour-on formulations are prepared by dissolving, suspending oremulsifying the active compound in suitable skin-compatible solvents orsolvent mixtures. If appropriate, other auxiliaries such as colorants,bioabsorption-promoting substances, antioxidants, light stabilizers,adhesives are added.

Suitable solvents are, for example, water, alkanols, glycols,polyethylene glycols, polypropylene glycols, glycerol, aromatic alcoholssuch as benzyl alcohol, phenylethanol, phenoxyethanol, esters such asethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkyl ethers such as dipropylene glycol monomethyl ether,diethylene glycol mono-butyl ether, ketones such as acetone, methylethyl ketone, cyclic carbonates such as propylene carbonate, ethylenecarbonate, aromatic and/or aliphatic hydrocarbons, vegetable orsynthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such asmethylpyrrolidone, n-butylpyrrolidone or n-octylpyrrolidone,N-methylpyrrolidone, 2-pyrrolidone,2,2-dimethyl-4-oxy-methylene-1,3-dioxolane and glycerol formal.

Suitable colorants are all colorants permitted for use on animals andwhich can be dissolved or suspended.

Suitable absorption-promoting substances are, for example, DMSO,spreading oils such as isopropyl myristate, dipropylene glycolpelargonate, silicone oils and copolymers thereof with polyethers, fattyacid esters, triglycerides, fatty alcohols.

Suitable antioxidants are, for example, sulfites or metabisulfites suchas potassium metabisulfite, ascorbic acid, butylhydroxytoluene,butylhydroxyanisole, tocopherol.

Suitable light stabilizers are, for example, novantisolic acid.

Suitable adhesives are, for example, cellulose derivatives, starchderivatives, polyacrylates, natural polymers such as alginates, gelatin.

Emulsions can be administered orally, dermally or as injections.

Emulsions are either of the water-in-oil type or of the oil-in-watertype.

They are prepared by dissolving the active compound either in thehydrophobic or in the hydrophilic phase and homogenizing this with thesolvent of the other phase with the aid of suitable emulsifiers and, ifappropriate, other auxiliaries such as colorants, absorption-promotingsubstances, preservatives, antioxidants, light stabilizers,viscosity-enhancing substances.

Suitable hydrophobic phases (oils) are, for example: liquid paraffins,silicone oils, natural vegetable oils such as sesame oil, almond oil,castor oil, synthetic triglycerides such as caprylic/capric biglyceride,triglyceride mixture with vegetable fatty acids of the chain lengthC₈-C₁₂ or other specially selected natural fatty acids, partialglyceride mixtures of saturated or unsaturated fatty acids possibly alsocontaining hydroxyl groups, mono- and diglycerides of the C₈-C₁₀ fattyacids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate,hexyl laurate, dipropylene glycol perlargonate, esters of a branchedfatty acid of medium chain length with saturated fatty alcohols of chainlength C₁₆-C₁₈, isopropyl myristate, isopropyl palmitate,caprylic/capric acid esters of saturated fatty alcohols of chain lengthC₁₂-C₁₈, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate,ethyl lactate, waxy fatty acid esters such as synthetic duck coccygealgland fat, dibutyl phthalate, diisopropyl adipate, and ester mixturesrelated to the latter, fatty alcohols such as isotridecyl alcohol,2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acidssuch as oleic acid and mixtures thereof.

Suitable hydrophilic phases are, for example, water, alcohols such aspropylene glycol, glycerol, sorbitol and mixtures thereof.

Suitable emulsifiers are, for example,

-   -   non-ionic surfactants, e.g. polyethoxylated castor oil,        polyethoxylated sorbitan monooleate, sorbitan monostearate,        glycerol monostearate, polyoxyethyl stearate, alkylphenol        polyglycol ether;    -   ampholytic surfactants such as di-sodium        N-lauryl-p-iminodipropionate or lecithin;    -   anionic surfactants, such as sodium lauryl sulfate, fatty        alcohol ether sulfates, mono/dialkyl polyglycol ether        orthophosphoric acid ester monoethanolamine salt;    -   cation-active surfactants, such as cetyltrimethylammonium        chloride.

Suitable further auxiliaries are substances which enhance the viscosityand stabilize the emulsion, such as carboxymethylcellulose,methylcellulose and other cellulose and starch derivatives,polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone,polyvinyl alcohol, copolymers of methyl vinyl ether and maleicanhydride, polyethylene glycols, waxes, colloidal silicic acid ormixtures of the substances mentioned.

Suspensions can be administered orally or topically/dermally. They areprepared by suspending the active compound in a suspending agent, ifappropriate with addition of other auxiliaries such as wetting agents,colorants, bioabsorption-promoting substances, preservatives,antioxidants, light stabilizers.

Liquid suspending agents are all homogeneous solvents and solventmixtures.

Suitable wetting agents (dispersants) are the emulsifiers given above.

Other auxiliaries, which may be mentioned, are those given above.

Semi-solid preparations can be administered orally ortopically/dermally. They differ from the suspensions and emulsionsdescribed above only by their higher viscosity.

For the production of solid preparations, the active compound is mixedwith suitable excipients, if appropriate with addition of auxiliaries,and brought into the desired form.

Suitable excipients are all physiologically tolerable solid inertsubstances. Those used are inorganic and organic substances. Inorganicsubstances are, for example, sodium chloride, carbonates such as calciumcarbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicicacids, argillaceous earths, precipitated or colloidal silica, orphosphates. Organic substances are, for example, sugar, cellulose,foodstuffs and feeds such as milk powder, animal meal, grain meals andshreds, starches.

Suitable auxiliaries are preservatives, antioxidants, and/or colorantswhich have been mentioned above.

Other suitable auxiliaries are lubricants and glidants such as magnesiumstearate, stearic acid, talc, bentonites, disintegration-promotingsubstances such as starch or crosslinked polyvinylpyrrolidone, binderssuch as starch, gelatin or linear polyvinylpyrrolidone, and dry binderssuch as microcrystalline cellulose.

In general, “parasitically effective amount” means the amount of activeingredient needed to achieve an observable effect on growth, includingthe effects of necrosis, death, retardation, prevention, and removal,destruction, or otherwise diminishing the occurrence and activity of thetarget organism. The parasitically effective amount can vary for thevarious compounds/compositions used in the invention. A parasiticallyeffective amount of the compositions will also vary according to theprevailing conditions such as desired parasiticidal effect and duration,target species, mode of application, and the like.

The compositions which can be used in the invention can comprisegenerally from about 0.001 to 95% of a compound of formula (I), astereoisomer, a tautomer or a salt thereof.

Generally it is favorable to apply the compounds of the presentinvention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably1 mg/kg to 50 mg/kg per day.

Ready-to-use preparations contain the compounds acting againstparasites, preferably ectoparasites, in concentrations of 10 ppm to 80percent by weight, preferably from 0.1 to 65 percent by weight, morepreferably from 1 to 50 percent by weight, most preferably from 5 to 40percent by weight.

Preparations which are diluted before use contain the compounds actingagainst ectoparasites in concentrations of 0.5 to 90 percent by weight,preferably of 1 to 50 percent by weight.

Furthermore, the preparations for controlling endoparasites comprise acompound of the present invention usually in concentrations of 10 ppm to2 percent by weight, preferably of 0.05 to 0.9 percent by weight, veryparticularly preferably of 0.005 to 0.25 percent by weight.

In a preferred embodiment of the present invention, the compositionscomprising the a compound of the present invention are applieddermally/topically.

In a further preferred embodiment, the topical application is conductedin the form of compound-containing shaped articles such as collars,medallions, ear tags, bands for fixing at body parts, and adhesivestrips and foils.

Generally it is favorable to apply solid formulations which releasecompounds of the present invention in total amounts of 10 mg/kg to 300mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160mg/kg body weight of the treated animal in the course of three weeks.

For the preparation of the shaped articles, thermoplastic and flexibleplastics as well as elastomers and thermoplastic elastomers are used.Suitable plastics and elastomers are polyvinyl resins, polyurethane,polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamidesand polyester which are sufficiently compatible with the compounds ofthe present invention. A detailed list of plastics and elastomers aswell as preparation procedures for the shaped articles is given e.g. inWO 03/086075.

The present invention is now illustrated in further details by thefollowing examples, without imposing any limitation thereto.

The following abbreviations are used:

TFA: trifluoroacetic acid

EtOAc: ethyl acetate

HPLC: High Performance Liquid Chromatography

MS: Mass spectrometry

MeOH: Methanol

The Compound examples were characterized by coupled High PerformanceLiquid Chromatography with mass spectrometry (HPLC/MS) or by theirmelting point.

Method A: Analytical HPLC column 1: RP-18 column Chromolith Speed ROD(from Merck KgaA, Germany). Elution: acetonitrile/water in a ratio offrom 5:95 to 95:5 in 5 minutes at 40° C.

Method B:

Analytical UPLC column: Phenomenex Kinetex 1.7 μm XB-C18 100A; 50×2.1mm; mobile phase: A: water; B: acetonitrile; gradient: 5-100% B in 1.50minutes; 100% B 0.20 min; flow: 0.8-1.0 mL/min in 1.50 minutes at 60° C.

MS-method: ESI positive.

A. PREPARATION EXAMPLES Example 1

(Compound example E1.2; (compound of formula I, wherein Het is6-chloropyridin-3-yl, —W¹-W²-W³-W⁴— represent —CH═CH—CH═CH—, X is O, R³is H, R⁵ is H and m is 0)

1.1 Synthesis of Amine Salt E1.1

A solution of 2-chloro-5-chloromethylpyridine (16.20 g, 100 mmol) and2-amino-pyridine (9.60 g, 102 mmol) in ethanol (100 mL) was refluxed for24 hours. The reaction was then cooled to room temperature, andconcentrated in vacuo. Then 100 mL of toluene were added to the residue,and the mixture was concentrated in vacuo. Then, 75 mL of CH₂Cl₂ wereadded to the residue and the mixture was rapidly stirred for 15 minutes,during which time a precipitate forms. The precipitate was thenfiltered, and washed with CH₂Cl₂ (50 mL), diethyl ether (50 mL), anddried under vacuum to afford the title product as a pale yellow solid(14.0 g, 55% yield).

LC-MS: mass calculated for C₁₁H₁₁ClN₃ [M]⁺ 220.1. found 220.1.t_(R)=0.529 min (t_(R): retention time)

1.2 Synthesis of Compound E1.2

To a suspension of amine salt E1.1 (1.50 g, 5.85 mmol), cyanoacetic acid(0.600 g, 7.05 mmol), and triethylamine (1.48 g, 14.65 mmol) indichloromethane (30 mL) at room temperature was added a solution ofpropyl phosphoric anhydride (2.23 g, 7.05 mmol, 50% by weight solutionin ethyl acetate). The reaction was then heated in the microwave at 100C for 3 hrs. The reaction was diluted with ethyl acetate (100 mL),washed with saturated aqueous NaHCO₃ (100 mL) and water (100 mL). Thelayers were separated, the organic layer dried over Na₂SO₄ and thenconcentrated in vacuo to afford a residue, which was purified usingcolumn chromatography over silica gel (0→30% MeOH/EtOAc) to afford thetitle product as a beige solid (0.520 g, 31% yield).

LC-MS: mass calculated for C₁₄H₁₂N₄OCl [M+H]⁺ 287.1. found 287.1.t_(R)=0.607 min.

Example 2

(Compound example E1.3; compound of formula I, wherein Het is6-chloropyridin-3-yl, —W¹-W²-W³-W⁴— represent —CH═CH—CH═CH—, X is O, R³and R⁵ together form with the carbon atom to which they are attachedform a cyclopropyl ring and m is 0)

To a suspension of amine salt E1.1 (6.00 g, 23.43 mmol),1-cyanocyclopropanecarboxylic acid (3.12 g, 28.10 mmol), andtriethylamine (5.93 g, 58.71 mmol) in CH₂Cl₂ (80 mL) at room temperaturewas added a solution of propyl phosphoric anhydride (8.95 g, 28.10 mmol,50% by weight solution in ethyl acetate). The reaction was then heatedin the microwave at 100 C for 3 hrs. The reaction was then diluted withethyl acetate (200 mL), washed with saturated aqueous NaHCO₃ (200 mL)and water (200 mL). The layers were separated, and the organic layerdried over Na₂SO₄ and concentrated in vacuo to afford a residue, whichwas purified using column chromatography over silica gel (0→30%MeOH/EtOAc), followed by preparative HPLC using 5%-95% CH₃CN/H₂O toafford the title product as a beige solid (0.130 g, 2% yield).

LC-MS: mass calculated for C₁₆H₁₄N₄OCl [M+H]⁺ 313.1. found 313.1.t_(R)=0.788 min.

By the method described above for example 1 and 2, the compounds offormula (I.A) summarized in table A.1 can be prepared.

TABLE A.1 (I.A)

RT m/z # HET R¹ R³ R⁵ method [min] [M + H]⁺ I.A-1 6-chloro-3- H H H B0.607 287.1 pyridyl I.A-2 6-chloro-3- CH₃ H H NMR* pyridyl I.A-36-chloro-3- CH₃ F F NMR* pyridyl I.A-4 2-chlorothiazol- H H H B 0.713292.7 5-yl I.A-5 tetrahydrofuran- H H H B 0.348 245.8 3-yl I.A-66-chloro-3- H CH₂CH₂CH₂CH₃ H B 0.937 343.7 pyridyl I.A-7 6-chloro-3- HCH₃ CH₃ B 0.845 315.5 pyridyl I.A-8 6-chloro-3- H CH₂CH₂CH₂ B 0.848326.8 pyridyl I.A-9 6-chloro-3- H CH₂CH₂CH₂CH₂ B 0.930 341.5 pyridylI.A-10 6-chloro-3- H C₆H₅ H B 0.927 362.7 pyridyl I.A-11 pyrimidin-5-ylH H H B 0.517 253.8 I.A-12 6-chloro-3- H allyl H B 0.922 326.4 pyridylI.A-13 6-chloro-3- H allyl allyl B 1.121 366.4 pyridyl I.A-146-chloro-3- H 2-methylallyl 2-methylallyl B 1.227 394.9 pyridyl I.A-156-chloro-3- H CH₂CH═CHCH₂ B 1.008 338.4 pyridyl I.A-16 6-chloro-3- H3-methylbut-2- H B 0.960 354.8 pyridyl enyl I.A-17 6-chloro-3- H3-methylbut-2- 3-methylbut-2- B 1.216 422.9 pyridyl enyl enyl I.A-186-chloro-3- H CH₂OCH₂ NMR* pyridyl I.A-19 2-chlorothiazol- H CH₂OCH₂NMR* 5-yl I.A-20 6-chloro-3- CH₃ CH₂OCH₂ NMR* pyridyl I.A-212-chlorothiazol- CH₃ CH₂OCH₂ NMR* 5-yl NMR* spectra: I.A-2Characterization by ¹H-NMR (400 MHz, CDCl₃): δ [delta] = 1.86 (d, 3H),3.49 (s, 2H), 6.74 (m, 1H), 7.30 (m, 1H), 7.57 (d. 1H), 7.65 (m, 1H),7.69-7.72 (m, 2H), 8.37 (d, 1H), 8.45 (d, 1H) ppm. I.A-3Characterization by ¹H-NMR (400 MHz, CDCl₃): δ [delta] = 1.92 (d, 3H),6.95 (dd, 1H), 7.15 (m, 1H), 7.38 (d. 1H), 7.66-7.73 (m, 2H), 7.83 (m,1H), 8.44 (d, 1H), 8.61 (d, 1H) ppm. I.A-18 Characterization by ¹H-NMR(400 MHz, CDCl₃): δ [delta] = 4.97 (d, 2H), 5.04 (d, 2H), 5.55 (s, 2H),6.81 (dd, 1H), 7.34 (d, 1H), 7.73-7.77 (m, 2H), 7.83 (m, 1H), 8.41 (d,1H), 8.54 (d, 1H) ppm. I.A-19 Characterization by ¹H-NMR (400 MHz,CDCl₃): δ [delta] = 5.05 (d, 2H), 5.17 (d, 2H), 5.60 (s, 2H), 6.82 (dd,1H), 7.65 (s, 1H), 7.74-7.77 (m, 2H), 8.57 (d, 1H) ppm. I.A-20Characterization by ¹H-NMR (400 MHz, CDCl₃): δ [delta] = 1.87 (d, 3H),4.98 (m, 2H), 5.08 (d, 2H), 6.79 (dd, 1H), 7.10 (m, 1H), 7.35 (d, 1H),7.61 (d, 1H), 7.65-7.71 (m, 2H), 8.42 (d, 1H), 8.53 (d, 1H) ppm. I.A-21Characterization by ¹H-NMR (400 MHz, CDCl₃): δ [delta] = 1.91 (d, 3H),5.01 (m, 2H), 5.14 (d, 2H), 6.80 (dd, 1H), 7.22 (m, 1H), 7.65-7.73 (m,3H), 8.52 (d, 1H) ppm.

By the method described above for example 1 and 2, the compounds offormula (I.B) summarized in table B.1 can be prepared.

TABLE B.1 (I.B)

RT m/z # Het R¹ R^(7b1) R^(7b2) R^(7b3) R^(7b4) method [min] [M + H]+I.B-1 6-chloro- H H H H H B 0.788 313.1 3-pyridyl I.B-2 6-chloro- CH₃ HH H H NMR* 3-pyridyl I.B-3 6-chloro- H CH₃ CH₃ CH₃ CH₃ B 0.981 369.63-pyridyl I.B-4 pyrimidin- H H H H H B 0.620 279.8 5-yl I.B-5 6-chloro-H H CH(CH₃)₂ H H B 1.042 354.8 3-pyridyl I.B-6 6-chloro- H HCH₂CH₂CH₂CH₃ H H B 1.102 368.9 3-pyridyl I.B-7 6-chloro- H H CH₂CH₂CH₃ HH B 1.030 354.8 3-pyridyl I.B-8 6-chloro- H H cC₃H₅ H H B 0.962 352.83-pyridyl I.B-9 6-chloro- H H CH₂CH₃ H H B 0.954 341.3 3-pyridyl I.B-106-chloro- H H cC₅H₉ H H B 1.105 380.9 3-pyridyl I.B-11 6-chloro- H H2-methyl- H H B 1.039 400.9 3-pyridyl sulfanylpropyl I.B-12 6-chloro- HH 2,2-dimethyl- H H B 1.134 382.9 3-pyridyl propyl I.B-13 6-chloro- H HCH₃ H H B 0.875 326.8 3-pyridyl I.B-14 6-chloro- H H 1-methylbutyl H H B1.150 382.9 3-pyridyl I.B-15 6-chloro- H H CH₂CH(CH₃)₂ H H B 1.086 368.93-pyridyl I.B-16¹⁾ 6-chloro- H H C₆H₅ H H B 1.017 389.4 3-pyridylI.B-17²⁾ 6 -chloro- H H C₆H₅ H B H 1.057 389.4 3-pyridyl I.B-186-chloro- H H phenethyl H H B 1.150 417.4 3-pyridyl I.B-19 6-chloro- H H1,2-dimethyl- H H B 1.221 397.4 3-pyridyl butyl I.B-20 6-chloro- H HTetrahydro- H H B 0.892 397.4 3-pyridyl pyran-4-yl I.B-21 6-chloro- H Hpentyl H H B 1.188 383.4 3-pyridyl I.B-22 6-chloro- H H cycloheptyl H HB 1.238 409.4 3-pyridyl I.B-23 6-chloro- H H non-3-enyl H H B 1.376437.5 3-pyridyl I.B-24 6-chloro- H H 1-ethylpentyl H H B 1.297 411.43-pyridyl I.B-25 6-chloro- H H 1,1-dimethyl-2- H H B 0.790 446.43-pyridyl (3-pyridyl)ethyl I.B-26 6-chloro- H H C(CH₃)₃ H H B 1.090369.4 3-pyridyl I.B-27 6-chloro- H H c-C₆H₁₁ H H B 1.184 395.5 3-pyridylI.B-28 6-chloro- H H 6,6-dimethyl- H H B 1.305 435.4 3-pyridylnorpinan-2-yl I.B-29 6-chloro- H H tetrahydro- H H B 1.064 413.43-pyridyl thiopyran-3-yl I.B-30 6-chloro- H H 3,3-dimethyl- H H B 1.229397.5 3-pyridyl butyl I.B-31 6-chloro- H H CF₃ H H B 1.028 381.33-pyridyl I.B-32 6-chloro- H H 1-acetoxyethyl H H B 0.932 399.43-pyridyl I.B-33 6-chloro- H H 1-isopropoxy- H H B 1.047 399.4 3-pyridylethyl I.B-34 6-chloro- H H 2-propoxyethyl H H B 1.050 399.4 3-pyridylI.B-35 6-chloro- H H 1-methyl-2- H H B 1.061 401.3 3-pyridylmethylsulfanyl- ethyl I.B-36 6-chloro- H H 2-methyl- H H B 1.181 407.43-pyridyl cyclohex-3-en- 1-yl I.B-37 6-chloro- H H 4-methyl- H H B 1.251409.3 3-pyridyl cyclohexyl I.B-38 6-chloro- H H 5,5-dimethyl- H H B1.011 410.9 3-pyridyl tetrahydrofuran- 2-yl I.B-39 6-chloro- H Htetrahydropyran- H H B 0.950 410.8 3-pyridyl 4-ylmethyl I.B-40 6-chloro-H H 2-isobutoxyethyl H H B 1.116 412.9 3-pyridyl I.B-41 6-chloro- H H1-(2-methoxy- H H B 0.918 414.8 3-pyridyl ethoxy)ethyl I.B-42 6-chloro-H H cyclooctyl H H B 1.263 422.9 3-pyridyl I.B-43 6-chloro- H H2-ethoxy- H H B 0.997 424.9 3-pyridyl carbonylcyclopropyl I.B-446-chloro- H H 1-methoxyethyl H H B 0.911 371.4 3-pyridyl I.B-456-chloro- H H 1,2-dimethyl- H H B 1.155 383.4 3-pyridyl propyl I.B-466-chloro- H H tetrahydropyran- H H B 0.918 397.4 3-pyridyl 3-yl I.B-476-chloro- H H 4-methylthiazol- H H B 0.866 409.8 3-pyridyl 5-yl I.B-486-chloro- H H tetrahydrothiopyran- H H B 1.085 426.9 3-pyridyl4-ylmethyl I.B-49¹⁾ 6-chloro- H H 1-phenoxyethyl H H B 1.127 432.93-pyridyl I.B-50 6-chloro- H H 1-(cyclohexoxy)ethyl H H B 1.198 438.93-pyridyl I.B-51 6-chloro- H H 6-methoxy-3- H H B 1.048 440.9 3-pyridylmethyl-tetra- hydropyran-2-yl I.B-52 6-chloro- H H (4-isopropyl- H H B1.400 451.0 3-pyridyl cyclohexyl) methyl I.B-53 6-chloro- H H6-acetoxyhexyl H H B 1.096 455.0 3-pyridyl I.B-54 6-chloro- H H3-(trifluoro- H H B 1.167 457.4 3-pyridyl methyl)phenyl I.B-55 6-chloro-H H 2-pyridyl H H B 0.743 390.4 3-pyridyl I.B-56¹⁾ 6-chloro- H H3-nitrophenyl H H B 1.023 433.9 3-pyridyl I.B-57²⁾ 6-chloro- H H3-nitrophenyl H H B 1.040 433.8 3-pyridyl I.B-58¹⁾ 6-chloro- H H4-(trifluoro- H H B 1.130 456.9 3-pyridyl methyl)phenyl I.B-59²⁾6-chloro- H H 4-(trifluoro- H H B 1.149 456.9 3-pyridyl methyl)phenylI.B-60 6-chloro- H CH₃ methoxycarbonyl H H B 0.899 385.4 3-pyridylI.B-61 6-chloro- H H benzyl H H B 1.096 403.4 3-pyridyl I.B-62 6-chloro-H H CH₂CF₃ H H B 1.011 395.1 3-pyridyl I.B-63 6-chloro- H Htetrahydrofuran- H H B 0.849 383.4 3-pyridyl 3-yl If not otherwiseindicated, the compounds of table B.1 are mixtures of cis-trans isomers.¹⁾Isomer 1 ²⁾Isomer 2 NMR* spectra: I.B-2 Characterization by ¹H-NMR(400 MHz, CD₃OD): δ [delta] = 1.48-1.56 (m, 4H), 1.93 (d, 3H), 6.93 (m,1H), 7.01 (m, 1H), 7.46 (d, 1H), 7.80 (m, 1H), 7.88 (m, 1H), 8.14-8.17(m, 2H), 8.51 (d, 1H) ppm.

By the method described above for example 1 and 2, the compounds offormula (I.C) summarized in table C.1 can be prepared.

TABLE C.1 (I.C)

RT m/z # HET R¹ R^(7b1) R^(7b2) [min] [M + H]+ method I.C-16-chloro-3-pyridyl H H H B 0.823 315.3

B. BIOLOGICAL EXAMPLES

The biological activity of the compounds of formula I of the presentinvention may be evaluated in biological tests as described in thefollowing.

General conditions: If not otherwise specified, most test solutions areto be prepared as follows: The active compound is to be dissolved at thedesired concentration in a mixture of 1:1 (vol:vol) distilledwater:acetone. Further, the test solutions are to be prepared at the dayof use (and, if not otherwised specified, in general at concentrationswt/vol).

B.1 Green Peach Aphid (Myzus persicae)

For evaluating control of green peach aphid (Myzus persicae) throughsystemic means, the test unit consists of 96-well-microtiter platescontaining liquid artificial diet under an artificial membrane.

The compounds are formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds arepipetted into the aphid diet, using a custom built pipetter, at tworeplications.

After application, 5-8 adult aphids are placed on the artificialmembrane inside the microtiter plate wells. The aphids are then allowedto suck on the treated aphid diet and incubated at about 23+1° C. andabout 50+5% relative humidity for 3 days. Aphid mortality and fecundityis then visually assessed.

In this test, compounds I.A-1, I.A-10, I.A-12, I.A-13, I.A-15, I.A-16,I.A-17, I.A-18, I.A-19, I.A-2, I.A-20, I.A-21, I.A-3, I.A-4, I.A-5,I.A-6, I.A-7, I.A-8, I.A-9, I.B-1, I.B-10, I.B-11, I.B-12, I.B-13,I.B-14, I.B-15, I.B-16, I.B-17, I.B-18, I.B-19, I.B-2, I.B-20, I.B-21,I.B-23, I.B-25, I.B-26, I.B-27, I.B-29, I.B-3, I.B-32, I.B-33, I.B-34,I.B-35, I.B-36, I.B-37, I.B-38, I.B-39, I.B-4, I.B-41, I.B-43, I.B-44,I.B-45, I.B-46, I.B-47, I.B-48, I.B-49, I.B-5, I.B-51, I.B-52, I.B-54,I.B-55, I.B-56, I.B-57, I.B-6, I.B-60, I.B-61, I.B-62, I.B-63, I.B-7,I.B-8, I.B-9, I.C-1 at 2500 ppm showed at least 75% mortality incomparison with untreated controls.

B.2 Vetch Aphid (Megoura viciae)

For evaluating control of vetch aphid (Megoura viciae) through contactor systemic means the test unit consisted of 24-well-microtiter platescontaining broad bean leaf disks.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the leaf disks at 2.5 μl, using a custom built microatomizer, at two replications.

After application, the leaf disks were air-dried and 5-8 adult aphidswere placed on the leaf disks inside the microtiter plate wells. Theaphids were then allowed to suck on the treated leaf disks and wereincubated at about 23±1° C. and about 50±5% relative humidity for 5days. Aphid mortality and fecundity was then visually assessed.

In this test, compounds I.A-1, I.A-10, I.A-12, I.A-13, I.A-14, I.A-15,I.A-16, I.A-18, I.A-19, I.A-2, I.A-20, I.A-21, I.A-3, I.A-4, I.A-6,I.A-7, I.A-8, I.A-9, I.B-1, I.B-10, I.B-11, I.B-12, I.B-13, I.B-14,I.B-15, I.B-16, I.B-17, I.B-19, I.B-2, I.B-20, I.B-21, I.B-25, I.B-26,I.B-29, I.B-3, I.B-32, I.B-33, I.B-34, I.B-35, I.B-36, I.B-37, I.B-38,I.B-39, I.B-4, I.B-41, I.B-43, I.B-44, I.B-45, I.B-46, I.B-47, I.B-48,I.B-49, I.B-5, I.B-50, I.B-53, I.B-54, I.B-55, I.B-56, I.B-6, I.B-60,I.B-61, I.B-62, I.B-63, I.B-7, I.B-8, I.B-9, I.C-1 at 2500 ppm showed atleast 75% mortality in comparison with Untreated Controls.

B.3 Cotton aphid (Aphis gossypii)

The active compound is dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:acetone. Surfactant (Alkamuls®EL 620) is added at a rate of 0.1% (vol/vol). The test solution isprepared at the day of use.

Potted cowpea plants were colonized with approximately 50-100 aphids ofvarious stages by manually transferring a leaf tissue cut from infestedplant 24 hours before application. Plants were sprayed after the pestpopulation has been recorded. Treated plants are maintained on lightcarts at about 28° C. Percent mortality was assessed after 72 hours.

In this test, compounds I.A-1, I.A-15, I.A-18, I.A-19, I.A-20, I.A-21,I.B-13 at 500 ppm showed over 75% mortality in comparison with untreatedcontrols.

B.4 Cowpea Aphid (Aphis craccivora)

The active compound is dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:acetone. Surfactant (Alkamuls®EL 620) is added at a rate of 0.1% (vol/vol). The test solution isprepared at the day of use.

Potted cowpea plants are colonized with approximately 50-100 aphids ofvarious stages by manually transferring a leaf tissue cut from infestedplant 24 hours before application. Plants are sprayed after the pestpopulation has been recorded. Treated plants are maintained on lightcarts at about 28° C. Percent mortality is assessed after 72 hours.

In this test, compounds I.A-1, I.A-10, I.A-12, I.A-13, I.A-15, I.A-16,I.A-18, I.A-19, I.A-2, I.A-20, I.A-21, I.A-5, I.A-6, I.A-7, I.A-8,I.B-1, I.B-13, I.B-2, I.B-4, I.B-7, I.B-8, I.B-9, I.C-1 at 500 ppmshowed at least 75% mortality in comparison with untreated controls.

B.5 Silverleaf Whitefly (bemisia argentifolii)

The active compounds are formulated in cyclohexanone as a 10,000 ppmsolution supplied in tubes. The tubes are inserted into an automatedelectrostatic sprayer equipped with an atomizing nozzle and they serveas stock solutions for which lower dilutions are made in 50% acetone:50%water (v/v). A nonionic surfactant (Kinetic®) is included in thesolution at a volume of 0.01% (v/v).

Cotton plants at the cotyledon stage (one plant per pot) are sprayed byan automated electrostatic plant sprayer equipped with an atomizingspray nozzle. The plants are dried in the sprayer fume hood and thenremoved from the sprayer. Each pot is placed into a plastic cup andabout 10 to 12 whitefly adults (approximately 3-5 days old) areintroduced. The insects are collected using an aspirator and a nontoxicTygon® tubing connected to a barrier pipette tip. The tip, containingthe collected insects, is then gently inserted into the soil containingthe treated plant, allowing insects to crawl out of the tip to reach thefoliage for feeding. Cups are covered with a reusable screened lid. Testplants are maintained in a growth room at about 25° C. and about 20-40%relative humidity for 3 days, avoiding direct exposure to fluorescentlight (24 hour photoperiod) to prevent trapping of heat inside the cup.Mortality is assessed 3 days after treatment, compared to untreatedcontrol plants.

In this test, compounds I.A-1, I.A-18, I.A-20, I.A-21, I.A-7, I.A-9,I.B-4 at 500 ppm showed at least 75% mortality in comparison withuntreated controls.

B.6 Orchid Thrips (dichromothrips corbetti)

Dichromothrips corbetti adults used for bioassay are obtained from acolony maintained continuously under laboratory conditions. For testingpurposes, the test compound is diluted in a 1:1 mixture of acetone:water(vol:vol), plus 0.01% vol/vol Alkamuls® EL 620 surfactant.

Thrips potency of each compound is evaluated by using a floral-immersiontechnique. Plastic petri dishes are used as test arenas. All petals ofindividual, intact orchid flowers are dipped into treatment solution andallowed to dry. Treated flowers are placed into individual petri dishesalong with about 20 adult thrips. The petri dishes are then covered withlids. All test arenas are held under continuous light and a temperatureof about 28° C. for duration of the assay. After 3 days, the numbers oflive thrips are counted on each flower, and along inner walls of eachpetri dish. The percent mortality is recorded 72 hours after treatment.

In this test, compounds I.A-1, I.A-18, I.A-19, I.A-2, I.A-20, I.A-21,I.A-3, I.A-4, I.A-6, I.A-7, I.B-1, I.B-11, I.B-13, I.B-2, I.B-3, I.B-5,I.B-9, I.C-1 at 500 ppm showed at least 75% mortality in comparison withuntreated controls.

B.7 Rice Green Leafhopper (Nephotettix virescens)

Rice seedlings are cleaned and washed 24 hours before spraying. Theactive compounds are formulated in 50:50 acetone:water (vol:vol), and0.1% vol/vol surfactant (EL 620) is added. Potted rice seedlings aresprayed with 5 ml test solution, air dried, placed in cages andinoculated with 10 adults. Treated rice plants are kept at about 28-29°C. and relative humidity of about 50-60%. Percent mortality is recordedafter 72 hours.

In this test, compounds I.A-1, I.A-10, I.A-12, I.A-18, I.A-19, I.A-2,I.A-20, I.A-21, I.A-3, I.A-4, I.A-6, I.A-7, I.A-8, I.A-9, I.B-1, I.B-10,I.B-11, I.B-13, I.B-15, I.B-2, I.B-4, I.B-5, I.B-7, I.B-8, I.B-9 at 500ppm showed at least 75% mortality in comparison with untreated controls.

B.8 Rice Brown Plant Hopper (Nilaparvata lugens)

Rice seedlings are cleaned and washed 24 hours before spraying. Theactive compounds is formulated in 50:50 acetone:water (vol:vol) and 0.1%vol/vol surfactant (EL 620) was added. Potted rice seedlings are sprayedwith 5 ml test solution, air dried, placed in cages and inoculated with10 adults. Treated rice plants are kept at about 28-29° C. and relativehumidity of about 50-60%. Percent mortality is recorded after 72 hours.

In this test, compounds I.A-1, I.A-18, I.A-2, I.A-20, I.A-3, I.A-4,I.A-6, I.A-7, I.A-8, I.B-1, I.B-13, I.B-2, I.B-4, I.B-8, I.B-9 at 500ppm showed at least 75% mortality in comparison with untreated controls.

B.9 Diamond Back Moth (Plutella xylostella)

The active compound is dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:aceteone. Surfactant (Alkamuls®EL 620) is added at a rate of 0.1% (vol/vol). The test solution isprepared at the day of use.

Leaves of cabbage were dipped in test solution and air-dried. Treatedleaves were placed in petri dish eslined with moist filter paper andinoculated with ten 3^(rd) instar larvae. Mortality was recorded 72hours after treatment. Feeding damages were also recorded using a scaleof 0-100%.

In this test, compounds I.A-18, I.A-2, I.A-7, I.B-1, I.B-9 at 500 ppmshowed over 75% mortality in comparison with untreated controls.

B.10 Green Soldier Stink Bug (Nezara viridula)

The active compound is dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:aceteone. Surfactant (KineticHV) is added at a rate of 0.01% (vol/vol). The test solution is preparedat the day of use.

Soybean pods were placed in microwavable plastic cups lined with moistfilter paper and inoculated with ten 3rd instar N. viridula. Using ahand atomizer, approximately 2 ml solution is sprayed into each cup.Treated cups were kept at about 28-29° C. and relative humidity of about50-60%. Percent mortality was recorded after 5 days.

In this test, compounds I.A-1, I.A-18, I.A-21 at 500 ppm showed over 75%mortality in comparison with untreated controls.

The invention claimed is:
 1. An N-acylimino compound of formula (I):

wherein m is an integer selected from 0, 1, 2, 3, 4, 5 or 6; X is O orS; Het is Het-1a

wherein # denotes the bond the remainder of the molecule in formula (I),R⁶ is selected from halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl and R^(6a)is hydrogen or halogen, in particular hydrogen wherein the moiety of theformula

represents a radical A selected from the group consisting of W.Het-1,W.Het-2, W.Het-3, W.Het-4:

wherein # denotes the bond to the remainder of the molecule, whereineach R^(w3), R^(w4), R^(w5), R^(w6) independently from each other, isselected from the group consisting of hydrogen, halogen, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkyl and C₁-C₄-haloalkyl; R¹, R² areindependently from each other selected from the group consisting ofhydrogen, halogen, cyano, and C₁-C₃-alkyl; R³ is selected from the groupconsisting of hydrogen, halogen, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, wherein each of the 4 last mentionedradicals are unsubstituted, partly or completely halogenated or carries1 or 2 radicals R⁷, it being also possible for cycloalkyl to carry 1, 2,3, 4, 5 or 6 C₁-C₄-alkyl groups, S(O)_(n)NR^(9a)R^(9b), NR^(9a)R^(9b),C(═O)OR⁸, C(═O)NR^(9a)R^(9b), C(═S)NR^(9a)R^(9b), C(═O)R^(7a),C(═S)R^(7a), NR^(9a)—C(═O)R^(7a), NR^(9a)—C(═S)R^(7a),NR^(9a)—S(O)_(n)R^(8a), phenyl, benzyl, where the phenyl ring in thelast two mentioned radicals is unsubstituted or may be substituted withone or more, e.g. 1, 2, 3, 4 or 5 identical or different substituentsR¹⁰, and a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated orunsaturated aromatic heterocyclic ring comprising 1, 2 or 3 heteroatomsas ring members, which are identical or different and selected fromoxygen, nitrogen and sulfur, where the heterocyclic ring is optionallysubstituted with 1, 2, 3 or 4 identical or different substituents R¹⁰,and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclicring may optionally be oxidized; R^(4a), R^(4b) are selected eachindependently from one another and independently from the integer of mfrom the group consisting of hydrogen, halogen, CN, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, and C₃-C₈-cycloalkyl, wherein each of thefour last mentioned radicals are unsubstituted, partly or completelyhalogenated, or R^(4a) and R^(4b) may form together with the carbon atomthey are bound to, a 3, 4, 5 or 6 membered aliphatic ring, wherein eachof the carbon atoms of the ring may be unsubstituted or may be partly orfully halogenated, and/or may carry 1, 2, 3, 4, 5 or 6 radicals selectedfrom C₁-C₄-alkyl, C₁-C₄-haloalky, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; orR^(4a) and R^(4b) may together form ═O, ═CR¹³R¹⁴, ═S, ═NR¹⁷, ═NOR¹⁶,═NNR^(9a)R^(9b), R⁵ is selected from the group consisting of hydrogen,halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,wherein each of the four last mentioned radicals are unsubstituted,partly or completely halogenated or carries 1 or 2 radicals R⁷, it beingalso possible for cycloalkyl radicals to carry 1, 2, 3, 4, 5 or 6C₁-C₄-alkyl groups, S(O)_(n)NR^(9a)R^(9b), NR^(9a)R^(9b), C(═O)OR⁸,C(═O)NR^(9a)R^(9b), C(═S)NR^(9a)R^(9b), C(═O)R^(7a), C(═S)R^(7a),NR^(9a)—C(═O)R^(7a), NR^(9a)—C(═S)R^(7a), NR^(9a)—S(O)_(n)R^(8a), amoiety Q-phenyl, where the phenyl ring is optionally substituted withone or more, e.g. 1, 2, 3, 4 or 5 identical or different substituentsR¹⁰, and a moiety Q-Het^(#), where Het^(#) represents a 3-, 4-, 5-, 6-or 7-membered saturated, partly saturated or unsaturated aromaticheterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members,which are selected from oxygen, nitrogen and/or sulfur, where theheterocyclic ring is optionally substituted with 1, 2, 3 or 4 identicalor different substituents R¹⁰, and wherein the nitrogen and/or thesulfur atom(s) of the heterocyclic ring may optionally be oxidized, andQ irrespectively of its occurrence, is a single bond, NR^(9a),NR^(9a)—C₁-C₄-alkylene, —O—C(═O)—, —NR^(9a)—C(═O)—, —O—S(═O)₂—,—NR^(9a)—S(═O)₂—, —O—C(═O)—C₁-C₄-alkylene or—NR^(9a)—C(═O)—C₁-C₄-alkylene, where the heteroatom in the last 6moieties is bound to the carbon atom of C(CN)R³ or CR^(4a)R^(4a),respectively; or, if m=0, R³ and R⁵ together may also form with thecarbon atom they are bound to, a 3, 4, 5 or 6 membered saturatedpartially unsaturated carbocycle or heterocycle, wherein the carbocycleor heterocycle may be unsubstituted or may carry 1, 2, 3, 4, 5 or 6radicals R^(7b), and where the heterocycle has 1 or 2 non-adjacentidentical or different heteroatoms or heteroatom moieties as ringmembers, which are selected from O, S, N and N—R^(17c), or R³ and R⁵ maytogether form ═O or ═S; where, independently of their occurrence, n is0, 1 or 2; R⁷ independently of its occurrence, is selected from thegroup consisting of cyano, azido, nitro, —SCN, SF₅, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆ haloalkynyl, Si(R¹¹)₂R¹², OR⁸,OSO₂R⁸, S(O)_(n)R⁸, S(O)_(n)NR^(17a)R^(17b), NR^(17a)R^(17b),C(═O)NR^(17a)R^(17b), C(═S)NR^(17a)R^(17b), C(═O)OR⁸, C(═O)R¹⁵,C(═S)R¹⁵, C(═NR¹⁷)R¹⁵, phenyl, phenyl-C₁-C₄-alkyl, where the phenyl ringin the last two groups is optionally substituted with 1, 2, 3, 4 or 5identical or different substituents R¹⁰, and a 3-, 4-, 5-, 6- or7-membered saturated, partly saturated or unsaturated aromaticheterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members,which are identical or different and selected from oxygen, nitrogen andsulfur, where the heterocyclic ring is optionally substituted with 1, 2,3 or 4 identical or different substituents R¹⁰, and wherein the nitrogenand/or the sulfur atom(s) of the heterocyclic ring may optionally beoxidized, or two R⁷ present on one carbon atom may together form ═O,═CR¹³R¹⁴, ═S, ═NR¹⁷, ═NOR¹⁶, ═NNR^(9a)R^(9b), or two R⁷ may form a 3-,4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclicor heterocyclic ring together with the carbon atoms to which the two R⁷are bonded, where the heterocyclic ring comprises 1, 2 or 3 heteroatomsas ring members, which are identical or different and selected fromoxygen, nitrogen and sulfur, where the heterocyclic ring is optionallysubstituted with 1, 2, 3 or 4 identical or different substituents R¹⁰;R^(7a) independently of its occurrence, is selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆ haloalkynyl, phenyl, optionally substituted with 1, 2, 3, 4 or 5identical or different substituents R¹⁰, and a 3-, 4-, 5-, 6- or7-membered saturated, partly saturated or unsaturated aromaticheterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members,which are identical or different and selected from oxygen, nitrogen andsulfur, where the heterocyclic ring is optionally substituted with 1, 2,3 or 4 identical or different substituents R¹⁰, and wherein the nitrogenand/or the sulfur atom(s) of the heterocyclic ring may optionally beoxidized; R^(7b) is selected from the group consisting of halogen,cyano, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₃-C₈-cycloalkenyl, and wherein the carbon atoms of the aforementionedaliphatic and cycloaliphatic radicals may be partly or completelyhalogenated, and/or be substituted with 1, 2,3 or 4, in particular 1, 2or 3, identical or different radicals R⁷, OR⁸, NR^(17a)R^(17b),S(O)_(n)R⁸, S(O)NR^(17a)R^(17b), C(O)R^(7a), C(O)NR^(17a)R^(17b),C(O)OR⁸, C(═S)R^(7a), C(═S)NR^(17a)R^(17b), C(═S)OR⁸, C(═NR¹⁷)R^(7a),C(═NR¹⁷)NR^(17a)R^(17b), Si(R¹¹)₂R¹²; phenyl, optionally substitutedwith 1, 2, 3, 4 or 5 identical or different substituents R¹⁰, and a 3-,4-, 5-, 6- or 7-membered saturated, partly saturated or unsaturatedaromatic heterocyclic ring comprising 1, 2 or 3 heteroatoms as ringmembers, which are identical or different and selected from oxygen,nitrogen and sulfur, where the heterocyclic ring is optionallysubstituted with 1, 2, 3 or 4 identical or different substituents R¹⁰,and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclicring may optionally be oxidized, or two of R^(7b) present on one ringcarbon may together form ═O, ═S or ═CR¹³R¹⁴, or two R^(7b) together forma linear C₂-C₇ alkylene chain, thus forming, together with the ringatom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-memberedring, where 1 or 2 CH₂ moieties of the alkylene chain may be replaced by1 or 2 heteroatom moieties selected from O, S and NR^(17c) and/or 1 or 2of the CH₂ groups of the alkylene chain may be replaced by a group C═O,C═S and/or C═NR¹⁷; and where the alkylene chain is unsubstituted or maybe substituted with 1, 2, 3, 4, 5 or 6 radicals selected from the groupconsisting of halogen, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, phenyl which may be substituted with 1, 2, 3, 4 or 5radicals R¹⁰, and a 3-, 4-, 5-, 6- or 7-membered saturated, partiallyunsaturated or aromatic heterocyclic ring containing 1, 2 or 3heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members, where the heterocyclic ring may be substituted with 1,2, 3, 4 or 5 radicals R¹⁰; R⁸ independently of its occurrence, isselected from the group consisting of hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆ haloalkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C(═O)R¹⁵,C(═O)NR^(17a)R^(17b), C(═S)NR^(17a)R^(17b), C(═O)OR¹⁶, phenyl,phenyl-C₁—C-₄-alkyl, where the phenyl ring in the last two mentionedradicals is unsubstituted or substituted with 1, 2, 3, 4 or 5 identicalor different substituents R¹⁰, and a 3-, 4-, 5-, 6- or 7-memberedsaturated, partly saturated or unsaturated aromatic heterocyclic ringcomprising 1, 2 or 3 heteroatoms as ring members, which are identical ordifferent and selected from oxygen, nitrogen and sulfur, where theheterocyclic ring is optionally substituted with 1, 2, 3 or 4 identicalor different substituents R¹⁰, and wherein the nitrogen and/or thesulfur atom(s) of the heterocyclic ring may optionally be oxidized,R^(8a) independently of its occurrence, is selected from the groupconsisting of C₁-C₆-alkyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein eachof the five last mentioned radicals are unsubstituted, partly orcompletely halogenated, phenyl, benzyl, where the phenyl ring in thelast two mentioned radicals is unsubstituted or may be substituted withone or more, e.g. 1, 2, 3, 4 or 5 identical or different substituentsR¹⁰, and a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated orunsaturated aromatic heterocyclic ring comprising 1, 2 or 3 heteroatomsas ring members, which are identical or different and selected fromoxygen, nitrogen and sulfur, where the heterocyclic ring is optionallysubstituted with 1, 2, 3 or 4 identical or different substituents R¹⁰,and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclicring may optionally be oxidized, R⁹ independently of its occurrence, isselected from the group consisting of hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆ haloalkynyl, phenyl, optionallysubstituted with 1, 2, 3, 4 or 5 identical or different substituentsR¹⁰; a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated orunsaturated aromatic C-bound heterocyclic ring comprising 1, 2 or 3heteroatoms as ring members, which are identical or different andselected from oxygen, nitrogen and sulfur, where the heterocyclic ringis optionally substituted with 1, 2, 3 or 4 identical or differentsubstituents R¹⁰, and wherein the nitrogen and/or the sulfur atom(s) ofthe heterocyclic ring may optionally be oxidized, R^(9a), R^(9b) areeach independently from one another selected from the group consistingof hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆ haloalkynyl,S(O)_(n)R¹⁶, —S(O)_(n)NR^(17a)R^(17b), C(═O)R¹⁵, C(═O)OR¹⁶,C(═O)NR^(17a)R^(17b), C(═S)R¹⁵, C(═S)SR¹⁶, C(═S)NR^(17a)R^(17b),C(═NR¹⁷)R¹⁵; phenyl, benzyl, 1-phenethyl or 2-phenethyl, where thephenyl ring in the last four mentioned radicals is unsubstituted or maybe substituted with 1, 2, 3, 4 or 5 identical or different substituentsR¹⁰; and a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated orunsaturated aromatic C-bound heterocyclic ring comprising 1, 2 or 3heteroatoms as ring members, which are identical or different andselected from oxygen, nitrogen and sulfur, where the heterocyclic ringis optionally substituted with 1, 2, 3 or 4 identical or differentsubstituents R¹⁰, and wherein the nitrogen and/or the sulfur atom(s) ofthe heterocyclic ring may optionally be oxidized, or, R^(9a) and R^(9b)are together a C₂-C₇ alkylene chain and form a 3-, 4-, 5-, 6-, 7- or8-membered saturated, partly saturated or unsaturated aromatic ringtogether with the nitrogen atom they are bonded to, wherein the alkylenechain may contain one or two heteroatoms, which are, independently ofeach other, selected from oxygen, sulfur or nitrogen, and where thealkylene chain may optionally be substituted with 1, 2, 3 or 4 radicalsselected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆ haloalkynyl, phenyl, optionallysubstituted with 1, 2, 3, 4 or 5 identical or different substituentsR¹⁰, and a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated orunsaturated aromatic C-bound heterocyclic ring comprising 1, 2 or 3heteroatoms as ring members, which are identical or different andselected from oxygen, nitrogen and sulfur, where the heterocyclic ringis optionally substituted with 1, 2, 3 or 4 identical or differentsubstituents R¹⁰, and wherein the nitrogen and/or the sulfur atom(s) ofthe heterocyclic ring may optionally be oxidized, or R^(9a) and R^(9b)together may form ═CR¹³R¹⁴, ═NR¹⁷, ═NOR¹⁶, ═NNR^(17a)R^(17b) moiety;R^(9c), R^(9d) are each independently from one another selected from thegroup consisting of hydrogen, C₁-C₆-alkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆ haloalkynyl, S(O)_(n)R¹⁶, —S(O)_(n)NR^(17a)R^(17b), C(═O)R¹⁵,C(═O)OR¹⁶, C(═O)NR^(17a)R^(17b), C(═S)R¹⁵, C(═S)SR¹⁶,C(═S)NR^(17a)R^(17b), C(═NR¹⁷)R¹⁵; phenyl, benzyl, where the phenyl ringin the last two mentioned radicals is unsubstituted or may besubstituted with 1, 2, 3, 4 or 5 identical or different substituentsR¹⁰; and a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated orunsaturated aromatic C-bound heterocyclic ring comprising 1, 2 or 3heteroatoms as ring members, which are identical or different andselected from oxygen, nitrogen and sulfur, where the heterocyclic ringis optionally substituted with 1, 2, 3 or 4 identical or differentsubstituents R¹⁰, and wherein the nitrogen and/or the sulfur atom(s) ofthe heterocyclic ring may optionally be oxidized; R¹⁰ independently ofits occurrence, is selected from the group consisting of halogen, cyano,azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,C₂-C₁₀-alkynyl, wherein the carbon atoms of the aforementioned aliphaticand cycloaliphatic radicals may optionally be substituted with 1, 2, 3,4 or 5 identical or different radicals R^(10a), Si(R¹¹)₂R¹², OR¹⁶,OS(O)_(n)R¹⁶, —S(O)_(n)R¹⁶, S(O)_(n)NR^(17a)R^(17b), NR^(17a)R^(17b),C(═O)R¹⁵, C(═S)R¹⁵, C(═O)OR¹⁶, —C(═NR¹⁷)R¹⁵, C(═O)NR^(17a)R^(17b),C(═S)NR^(17a)R^(17b), phenyl, optionally substituted with 1, 2, 3, 4 or5 identical or different radicals selected from OH, halogen, cyano,nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy,and a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated orunsaturated aromatic heterocyclic ring comprising 1, 2 or 3 heteroatomsas ring members, which are identical or different and selected fromoxygen, nitrogen and sulfur, where the heterocyclic ring isunsubstituted or may be substituted with 1, 2, 3, 4 or 5 substituentsselected independently from one another from halogen, cyano, NO₂,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, andwherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ringmay optionally be oxidized; or two R¹⁰ present together on one carbonring atom of a saturated or partly unsaturated heterocyclic radical mayform ═O, ═CR¹³R¹⁴, ═S, ═NR¹⁷, ═NOR¹⁶, ═NNR^(17a)R^(17b); or, two R¹⁰ onadjacent carbon ring atoms may also be a bivalent radical selected fromCH₂CH₂CH₂CH₂, CH═CH—CH═CH, N═CH—CH═CH, CH═N—CH═CH, N═CH—N═CH,OCH₂CH₂CH₂, OCH═CHCH₂, CH₂OCH₂CH₂, OCH₂CH₂O, OCH₂OCH₂, CH₂CH₂CH₂,CH═CHCH₂, CH₂CH₂O, CH═CHO, CH₂OCH₂, CH₂C(═O)O, C(═O)OCH₂, O(CH₂)O,SCH₂CH₂CH₂, SCH═CHCH₂, CH₂SCH₂CH₂, SCH₂CH₂S, SCH₂SCH₂, CH₂CH₂S, CH═CHS,CH₂SCH₂, CH₂C(═S)S, C(═S)SCH₂, S(CH₂)S, CH₂CH₂NR¹⁷, CH₂CH═N, CH═CH—NR¹⁷,OCH═N, SCH═N and form together with the carbon atoms to which the twoR¹⁰ are bonded to a 5-membered or 6-membered partly saturated orunsaturated, aromatic carbocyclic or heterocyclic ring, wherein the ringmay optionally be substituted with one or two substituents selected from═O, OH, CH₃, OCH₃, halogen, cyano, halomethyl and halomethoxy; R^(10a)independently of its occurrence, is selected from the group consistingof halogen, cyano, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, Si(R¹¹)₂R¹², OR¹⁶, OS(O)_(n)R¹⁶, —S(O)_(n)R¹⁶,S(O)_(n)NR^(17a)R^(17b), NR^(17a)R^(17b), C(═O)R¹⁵, C(═S)R¹⁵, C(═O)OR¹⁶,—C(═NR¹⁷)R¹⁵, C(═O)NR^(17a)R^(17b), C(═S)NR^(17a)R^(17b), phenyl,optionally substituted with 1, 2, 3, 4 or 5 identical or differentradicals selected from OH, halogen, cyano, nitro, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; R¹¹, R¹²independently of their occurrence, are selected from the groupconsisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,C₃-C₈-halocycloalkyl-C₁-C₄-alkyl, C₁-C₆-haloalkoxy-C₁-C₄-alkyl, phenyland benzyl, where the phenyl ring in last two radicals are unsubstitutedor substituted with 1, 2, 3, 4 or 5 identical or different radicalsselected from halogen, OH, cyano, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; R¹³, R¹⁴ independently of theiroccurrence, are selected from the group consisting of hydrogen, halogen,CN, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl andbenzyl; R¹⁵ independently of its occurrence, is selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₈-cycloalkyl, wherein the four last mentioned aliphatic andcycloaliphatic radicals may be unsubstituted, partially or fullyhalogenated and/or oxygenated and/or may carry 1 or 2 radicals selectedfrom C₁-C₄ alkoxy; phenyl, benzyl and pyridyl, wherein the last threeradicals may be unsubstituted, partially or fully halogenated and/or tocarry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆ haloalkoxy, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)amino or di-(C₁-C₆-alkyl)amino; R¹⁶ independently of itsoccurrence, is selected from the group consisting of hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl, wherein the five last mentioned aliphaticand cycloaliphatic radicals may be unsubstituted, partially or fullyhalogenated and/or oxygenated and/or may carry 1 or 2 radicals selectedfrom C₁-C₄ alkoxy, phenyl, benzyl and pyridyl, wherein the last threeradicals may be unsubstituted, partially or fully halogenated and/or tocarry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆ haloalkoxy, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)amino or di-(C₁-C₆-alkyl)amino; R¹⁷ independently of itsoccurrence, is selected from the group consisting of hydrogen,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, trimethylsilyl,triethylsilyl, tertbutyldimethylsilyl, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, wherein the four last mentionedaliphatic and cycloaliphatic radicals may be unsubstituted, partially orfully halogenated and/or oxygenated and/or may carry 1 or 2 radicalsselected from C₁-C₄-alkoxy, phenyl, benzyl, pyridyl, phenoxy, whereinthe four last mentioned radicals may be unsubstituted, partially orfully halogenated and/or carry 1, 2 or 3 substituents selected fromC₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy and(C₁-C₆-alkoxy)carbonyl, R^(17a), R^(17b) are each independently from oneanother selected from the group consisting of hydrogen, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylthio, trimethylsilyl, triethylsilyl,tertbutyldimethylsilyl, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₈-cycloalkyl, wherein the four last mentioned aliphatic andcyclo-aliphatic radicals may be unsubstituted, partially or fullyhalogenated and/or oxygenated and/or may carry 1 or 2 radicals selectedfrom C₁-C₄-alkoxy, phenyl, benzyl, pyridyl, phenoxy, wherein the fourlast mentioned radicals may be unsubstituted, partially or fullyhalogenated and/or carry 1, 2 or 3 substituents selected fromC₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy and(C₁-C₆-alkoxy)carbonyl, or, R^(17a) and R^(17b) may together be a C₂-C₆alkylene chain forming a 3- to 7-membered saturated, partly saturated orunsaturated ring together with the nitrogen atom R^(17a) and R^(17b) arebonded to, wherein the alkylene chain may contain 1 or 2 heteroatomsselected, independently of each other, from oxygen, sulfur or nitrogen,and may optionally be substituted with halogen, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, and wherein the nitrogen and/or thesulfur atom(s) of the heterocyclic ring may optionally be oxidized; orR^(17a) and R^(17b) together may form ═CR¹³R¹⁴, ═NR¹⁷ or ═NOR¹⁶ moiety;R^(17c) independently of its occurrence, is selected from the groupconsisting of hydrogen, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, wherein the five lastmentioned aliphatic and cycloaliphatic radicals may be unsubstituted,partially or fully halogenated and/or oxygenated and/or may carry 1 or 2radicals selected from C₁-C₄ alkoxy, phenyl, benzyl and pyridyl, whereinthe last three radicals may be unsubstituted, partially or fullyhalogenated and/or to carry 1, 2 or 3 substituents selected fromC₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy,(C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)amino or di-(C₁-C₆-alkyl)amino; thestereoisomers, tautomers and the salts thereof.
 2. The compound of claim1, wherein at least one of the radicals R₁ and R₂ is hydrogen.
 3. Thecompound of claim 2, wherein both R¹ and R² are hydrogen.
 4. Thecompound of claim 1, wherein R³ is selected from the group consisting ofhydrogen, halogen, CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, NR^(9a)R^(9b) and NR^(9a)—C(═O)R^(7a).
 5. Thecompound of claim 4, wherein R³ is selected from the group consisting ofhydrogen, fluorine, chlorine, C₁-C₄-alkyl, NHC(═O)—C₁-C₄-alkyl and CN.6. The compound of claim 1, wherein m is 0 or
 1. 7. The compound ofclaim 1, wherein m is 1, and R^(4a), R^(4b) are selected independentlyfrom one another from hydrogen, methyl and halogen or R^(4a) and R^(4b)together are ═O.
 8. The compound of claim 1, wherein R⁵ is hydrogen,halogen, CN, NR^(9a)R^(9b), C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C(═O)OR⁸, C(═O)NR^(9a)R^(9b),C(═S)NR^(9a)R^(9b), C(═O)R^(7a), C(═S)R^(7a), Q-phenyl, where phenyl isunsubstituted or substituted with 1, 2, 3, 4 or 5 identical or differentsubstituents R¹⁰, or Q-Het^(#), where Het^(#) is unsubstituted orsubstituted with 1, 2, 3, 4 or 5 identical or different substituentsR¹⁰, and where Q, irrespectively of its occurrence, is a bond, NR^(9a),NR^(9a)—C(═O), OC(═O), NR^(9a)CH₂, OC(═O)CH₂, or NR^(9a)C(═O)CH₂.
 9. Thecompound of claim 1, wherein R⁵ is hydrogen, halogen, CN, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl and phenyl,which is unsubstituted or carries 1, 2, 3, 4 or 5 identical or differentsubstituents R¹⁰.
 10. The compound of claim 1, wherein m is 0, and R³and R⁵ together with the carbon atom, to which they are bound, form a 3,4, 5 or 6 membered saturated carbocyle, wherein the carbocycle may beunsubstituted or may carry 1, 2, 3, 4, 5 or 6 radicals R^(7b), or R³ andR⁵ together with the carbon atom, to which they are bound, form a 3, 4,5 or 6 membered saturated heterocycle having 1 or 2 non adjacentheteroatoms as ring members which are selected from O and S, wherein theheterocycle may be unsubstituted or may carry 1, 2, 3, 4, 5 or 6radicals R^(7b), wherein R^(7b) is selected from the group consisting ofhalogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, and C₂-C₆-alkynyl, and wherein thecarbon atoms of the aforementioned aliphatic radicals may optionally bepartly or completely halogenated, and wherein one or two radicals R^(7b)may also be C₃-C₆-cycloalkyl, which is unsubstituted or carries 1, 2, 3,4 or 5 radicals selected from fluorine, chlorine or methyl, phenyl,optionally substituted with 1, 2, 3, 4 or 5 identical or differentsubstituents R^(10a), or a a 3-, 4-, 5-, 6- or 7-membered saturated,partly saturated or unsaturated aromatic heterocyclic ring comprising 1,2 or 3 heteroatoms as ring members, which are identical or different andselected from oxygen, nitrogen and sulfur, where the heterocyclic ringis optionally substituted with 1, 2, 3 or 4 identical or differentsubstituents R^(10a), and wherein the nitrogen and/or the sulfur atom(s)of the heterocyclic ring may optionally be oxidized, or two of R^(7b)present on one ring carbon may together form ═O or ═S, or two R^(7b)together form a linear C₂-C₇ alkylene chain, thus forming, together withthe carbon atom to which they are bound, a 3-, 4-, 5- or 6-memberedring, where 1 or 2 CH₂ moieties of the alkylene chain may be replaced by1 or 2 heteroatom moieties selected from O and S, and where the alkylenechain is unsubstituted or may be substituted with 1, 2, 3, 4, 5 or 6radicals selected from the group consisting of halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, R^(10a) is selectedfrom the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; or R³ and R⁵ together form ═O. 11.The compound of claim 10, wherein R³ and R⁵ together with the carbonatom, to which they are bound, form a 3 or 4 membered saturatedcarbocyle, wherein the carbocycle may be unsubstituted or may carry 1,2, 3, 4, 5 or 6 radicals R^(7b), or R³ and R⁵ together with the carbonatom, to which they are bound, form a 3, 4, 5 or 6 membered saturatedheterocycle having 1 or 2 non adjacent heteroatoms as ring members whichare selected from O and S, wherein the heterocycle may be unsubstitutedor may carry 1, 2, 3, 4, 5 or 6 radicals R^(7b), wherein R^(7b) isselected from the group consisting of halogen, C₁-C₄-alkyl, and whereinone radical R^(7b) may also be phenyl, optionally substituted with 1, 2,3, 4 or 5 identical or different substituents R^(10a), where R^(10a) isselected from the group consisting of halogen, CN, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.
 12. The compound ofclaim 1, wherein the radical A is W.Het-2.
 13. The compound of claim 12,wherein R^(w5) is hydrogen.
 14. The compound of claim 1, wherein m is 0or 1; R¹, R² are independently from each other selected from the groupconsisting of hydrogen, halogen, CN, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-halocycloalkyl; or R¹ and R² may together be═CR¹³R¹⁴; or R¹ and R² form, together with the carbon atom, which theyattached to, a 3- to 5-membered saturated carbocyclic ring; R³ isselected from the group consisting of hydrogen, halogen, CN,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,NR^(9a)R^(9b) and NR^(9a)—C(═O)R^(7a); R⁵ is hydrogen, halogen, CN,NR^(9a)R^(9b), C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C(═O)OR⁸, C(═O)NR^(9a)R^(9b), C(═S)NR^(9a)R^(9b), C(═O)R^(7a),C(═S)R^(7a), Q-phenyl, where phenyl is unsubstituted or substituted with1, 2, 3, 4 or 5 identical or different substituents R¹⁰, or Q-Het^(#),where Het^(#) is unsubstituted or substituted with 1, 2, 3, 4 or 5identical or different substituents R¹⁰, and where Q, irrespectively ofits occurrence, is a bond, NR^(9a), NR^(9a)—C(═O), OC(═O), NR^(9a)CH₂,OC(═O)CH₂, or NR^(9a)C(═O)CH₂, if m is 1, R^(4a), R^(4b) are selectedindependently from one another from hydrogen, methyl and halogen orR^(4a) and R^(4b) together are ═O, or if m is 0, R³ and R⁵ together withthe carbon atom, to which they are bound, form a 3, 4, 5 or 6 memberedsaturated carbocyle, wherein the carbocycle may be unsubstituted or maycarry 1, 2, 3, 4, 5 or 6 radicals R^(7b), or R³ and R⁵ together with thecarbon atom, to which they are bound, form a 3, 4, 5 or 6 memberedsaturated heterocycle having 1 or 2 non adjacent heteroatoms as ringmembers which are selected from O and S, wherein the heterocycle may beunsubstituted or may carry 1, 2, 3, 4, 5 or 6 radicals R^(7b), whereinR^(7b) is selected from the group consisting of halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, and C₂-C₆-alkynyl, and wherein the carbon atoms of theaforementioned aliphatic radicals may optionally be partly or completelyhalogenated, and wherein one or two radicals R^(7b) may also beC₃-C₆-cycloalkyl, which is unsubstituted or carries 1, 2, 3, 4 or 5radicals selected from fluorine, chlorine or methyl, phenyl, optionallysubstituted with 1, 2, 3, 4 or 5 identical or different substituentsR^(10a), or a a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturatedor unsaturated aromatic heterocyclic ring comprising 1, 2 or 3heteroatoms as ring members, which are identical or different andselected from oxygen, nitrogen and sulfur, where the heterocyclic ringis optionally substituted with 1, 2, 3 or 4 identical or differentsubstituents R^(10a), and wherein the nitrogen and/or the sulfur atom(s)of the heterocyclic ring may optionally be oxidized, or two of R^(7b)present on one ring carbon may together form ═O or ═S, or two R^(7b)together form a linear C₂-C₇ alkylene chain, thus forming, together withthe carbon atom to which they are bound, a 3-, 4-, 5- or 6-memberedring, where 1 or 2 CH₂ moieties of the alkylene chain may be replaced by1 or 2 heteroatom moieties selected from O and S, and where the alkylenechain is unsubstituted or may be substituted with 1, 2, 3, 4, 5 or 6radicals selected from the group consisting of halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, R^(10a) is selectedfrom the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; or R³ and R⁵ together form ═O. 15.The compound of claim 1, wherein both R¹ and R² are hydrogen; R³ isselected from the group consisting of hydrogen, fluorine, chlorine,C₁-C₄-alkyl, NHC(═O)—C₁-C₄-alkyl and CN; R⁵ is hydrogen, halogen, CN,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl andphenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 identical ordifferent substituents R¹⁰; if m is 1, R^(4a), R^(4b) are each hydrogenor R^(4a) and R^(4b) together are ═O, or if m is 0, R³ and R⁵ togetherwith the carbon atom, to which they are bound, form a 3 or 4 memberedsaturated carbocyle, wherein the carbocycle may be unsubstituted or maycarry 1, 2, 3, 4, 5 or 6 radicals R^(7b), wherein or R³ and R⁵ togetherwith the carbon atom, to which they are bound, form a 3, 4, 5 or 6membered saturated heterocycle having 1 or 2 non adjacent heteroatoms asring members which are selected from O and S, wherein the heterocyclemay be unsubstituted or may carry 1, 2, 3, 4, 5 or 6 radicals R^(7b),R^(7b) is selected from the group consisting of halogen, C₁-C₄-alkyl,and wherein one radical R^(7b) may also be phenyl, optionallysubstituted with 1, 2, 3, 4 or 5 identical or different substituentsR^(10a), where R^(10a) is selected from the group consisting of halogen,CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy. 16.The compound of claim 1, wherein X is O.
 17. An agricultural orveterinary composition for combating animal pests comprising at leastone compound of claim 1, and at least one inert liquid and/or solidacceptable carrier and optionally, if desired, at least one surfactant.18. A method for combating or controlling invertebrate pests, comprisingcontacting said pest or its food supply, habitat or breeding groundswith a pesticidally effective amount of at least one compound ofclaim
 1. 19. A method for protecting growing plants from attack orinfestation by invertebrate pests, comprising contacting a plant, orsoil or water in which the plant is growing, with a pesticidallyeffective amount of at least one compound of claim
 1. 20. A method forthe protection of plant propagation material from soil insects and ofthe seedlings roots and shoots from soil and foliar insects comprisingcontacting the plant propagation material before sowing and/or afterpregermination with at least one compound of claim
 1. 21. A method fortreating animals infested or infected by parasites or preventing animalsof getting infected or infested by parasites or protecting animalsagainst infestation or infection by parasites comprising administeringor applying to the animals a parasiticidally effective amount of thecompound of claim 1.